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N-Methyl dicyclohexylamine → HCID 86731498, compound

HRID 1773039
Notes
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Reaction equation

HRID 1773039 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([CH3:46])([CH3:45])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:44])([C@@:13]3([CH3:43])[C@H:18]([CH2:19][CH2:20]1)[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([NH:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][S:38](=[O:42])(=[O:41])[CH2:37][CH2:36]1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=O)=O.[C:49]([O:53][C:54]([NH:56][C:57]1([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:59][CH:58]1[CH:60]=[CH2:61])=[O:55])([CH3:52])([CH3:51])[CH3:50].C1(N(C)C2CCCCC2)CCCCC1>O1CCOCC1.C(OCC)C.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:49]([O:53][C:54]([NH:56][C:57]1([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:59][CH:58]1/[CH:60]=[CH:61]/[C:7]1[C:8]([CH3:46])([CH3:45])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:44])([C@@:13]3([CH3:43])[C@H:18]([CH2:19][CH2:20]1)[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([NH:32][CH2:33][CH2:34][N:35]1[CH2:36][CH2:37][S:38](=[O:42])(=[O:41])[CH2:39][CH2:40]1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)=[O:55])([CH3:52])([CH3:50])[CH3:51]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 24210N-Methyl dicyclohexylamineHCID 22091725Ethyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylateHCID 71698666(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate

Product 1

HCID 86731498
HCID 86731498, compound

Reagents, catalysts & solvents 3

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate (50 mg, 0.070 mmol), ethyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate (17.76 mg, 0.070 mmol) and N-cyclohexyl-N-methylcyclohexanamine (0.018 mL, 0.083 mmol) in dioxane (1 mL) was placed in a sealable pressure tube and N2 was bubbled through the solution for 10 min. Bis(tri-tertbutylphosphine) Palladium(0) (0.355 mg, 0.695 μmol) was added to the reaction mixture and the tube was sealed, and heated to 110° C. for 4 h. After cooling to rt, the crude reaction mixture was diluted with diethyl ether and filtered. The filtrate was concentrated and purified using a flash silica gel column (4 g; eluted with ethyl acetate in hexane from 0 to 45%) to give the title compound as a yellow film (13 mg, 22.7%). MS: m/e 824.55 (M+H)+, 2.625 min (method 4). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.23-5.36 (m, 2H), 5.27-5.12 (m, 1H), 4.72 (br. s., 1H), 4.61 (br. s., 1H), 4.26 (m, 2H), 3.24-2.92 (m, 8H), 2.72-2.45 (m, 5H), 2.32-1.76 (m, 11H), 1.68 (br. s., 3H), 1.53-0.74 (m, 42H).

Workup

  1. customwas placed in a sealable pressure tube
  2. customN2 was bubbled through the solution for 10 min
  3. customthe tube was sealed
  4. temperatureAfter cooling to rt
  5. customthe crude reaction mixture
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified
  9. washa flash silica gel column (4 g; eluted with ethyl acetate in hexane from 0 to 45%)

Sources & evidence

ORD record
ord-d99f292f65b640ccb0a97401ad9c2ad8
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249180B2

Reaction notes

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