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Diisopropylethylamine → HCID 86340152, compound

HRID 2275028
Notes
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Reaction equation

HRID 2275028 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3=[N:10][CH:11]=[CH:12][CH:13]=[C:8]3[CH:7]=[C:6]2[C:14]2[N:18]([CH3:19])[C:17]3[C:20]([O:27][CH3:28])=[CH:21][C:22]([C:24]([OH:26])=O)=[CH:23][C:16]=3[N:15]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:62]([O:66][C:67](=[O:76])[NH:68][C@@H:69]1[C@H:74]([OH:75])[CH2:73][CH2:72][NH:71][CH2:70]1)([CH3:65])([CH3:64])[CH3:63]>CN(C=O)C.CCOCC.O>[C:62]([O:66][C:67](=[O:76])[NH:68][C@@H:69]1[C@H:74]([OH:75])[CH2:73][CH2:72][N:71]([C:24]([C:22]2[CH:21]=[C:20]([O:27][CH3:28])[C:17]3[N:18]([CH3:19])[C:14]([C:6]4[N:5]([CH2:4][CH:1]5[CH2:2][CH2:3]5)[C:9]5=[N:10][CH:11]=[CH:12][CH:13]=[C:8]5[CH:7]=4)=[N:15][C:16]=3[CH:23]=2)=[O:26])[CH2:70]1)([CH3:65])([CH3:63])[CH3:64]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 863401542-(1-(Cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carboxylic acidHCID 86340187tert-Butyl ((3S,4R)-4-hydroxypiperidin-3-yl)carbamate

Product 1

HCID 86340152
HCID 86340152, compound
Yield 91%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carboxylic acid (105 mg, 0.279 mmol) in DMF (1.5 mL) was added HATU (106 mg, 0.279 mmol) followed by DIPEA (0.097 mL, 0.558 mmol) and the reaction stirred at room temperature for 15 min. tert-Butyl((3S,4R)-4-hydroxypiperidin-3-yl)carbamate (60.3 mg, 0.279 mmol) was added in DMF (1.5 mL) and the reaction stirred at RT for 16 h. LCMS showed complete reaction. Water (20 mL) and Et2O (20 mL) were added and the layers separated. The aqueous layer was extracted with further Et2O (2×20 mL) and the combined organics washed with water (2×20 mL), dried (Na2SO4) and concentrated in vacuo to afford a yellow oil. The crude product was purified by flash chromatography on silica (10 g) using a gradient of DCM→100% (20% MeOH/DCM)/DCM. The appropriate fractions were combined and evaporated under vacuum to give the product as a yellow oil—tert-butyl((3S,4R)-1-(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)-4-hydroxypiperidin-3-yl)carbamate (146 mg, 0.254 mmol, 91% yield).

Workup

  1. customreaction
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with further Et2O (2×20 mL)
  4. washthe combined organics washed with water (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil
  8. customThe crude product was purified by flash chromatography on silica (10 g)
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-be2b26d346e947f2ad5b7053df94139a
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09127003B2

Reaction notes

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