Diisopropylethylamine → HCID 86676637, compound

HRID 85722Notes

Reaction equation

HRID 85722 reaction equation
Cl[CH2:2][CH2:3][NH:4][C@:5]12[CH2:40][CH2:39][C@@H:38]([C:41]([CH3:43])=[CH2:42])[C@@H:6]1[C@@H:7]1[C@@:20]([CH3:23])([CH2:21][CH2:22]2)[C@@:19]2([CH3:24])[C@@H:10]([C@:11]3([CH3:37])[C@@H:16]([CH2:17][CH2:18]2)[C:15]([CH3:26])([CH3:25])[C:14]([C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=2)=[CH:13][CH2:12]3)[CH2:9][CH2:8]1.CCN(C(C)C)C(C)C.[N:53]1([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>CS(C)=O>[CH3:34][O:33][C:31]([C:30]1[CH:29]=[CH:28][C:27]([C:14]2[C:15]([CH3:25])([CH3:26])[C@H:16]3[C@:11]([CH3:37])([CH2:12][CH:13]=2)[C@@H:10]2[C@:19]([CH3:24])([C@@:20]4([CH3:23])[C@H:7]([CH2:8][CH2:9]2)[C@H:6]2[C@H:38]([C:41]([CH3:43])=[CH2:42])[CH2:39][CH2:40][C@:5]2([NH:4][CH2:3][CH2:2][N:56]2[CH2:57][CH2:58][N:53]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:54][CH2:55]2)[CH2:22][CH2:21]4)[CH2:18][CH2:17]3)=[CH:36][CH:35]=1)=[O:32]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86676636methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-chloroethyl)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)benzoate

Product 1

HCID 86676637HCID 86676637, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-chloroethyl)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)benzoate (230 mg, 0.379 mmol), Hunig's Base (0.331 mL, 1.895 mmol) and tert-butyl piperazine-1-carboxylate (141 mg, 0.759 mmol) in DMSO (3 mL) was heated up at 120° C. for 1 hour. The reaction mixture was quenched with water (10 mL), extracted with ethyl acetate (3×8 mL), the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the crude, the crude was purified by silica gel chromatography with 0-30% ethyl acetate/hexanes to provide the desired product as a white solid (150 mg, 52%). LCMS: m/e 756.66 (M+H)+, 2.50 min (method 11).

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with ethyl acetate (3×8 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto provide the crude
  7. customthe crude was purified by silica gel chromatography with 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7b9d0f59e4cc47239b80d396162c078b
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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