Dimethylformamide → HCID 66576762, compound

HRID 1409411Notes

Reaction equation

HRID 1409411 reaction equation
[OH:1][C:2]([C:5]1[NH:9][N:8]=[C:7]([C:10]([OH:12])=O)[CH:6]=1)([CH3:4])[CH3:3].[NH2:13][C@@H:14]([CH3:30])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[CH:22]=2)=[N:17]1.CN(C=O)C>O>[Cl:29][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][N:16]([CH2:15][C@@H:14]([NH:13][C:10]([C:7]3[CH:6]=[C:5]([C:2]([OH:1])([CH3:3])[CH3:4])[NH:9][N:8]=3)=[O:12])[CH3:30])[N:17]=2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 58810641HCID 58810641, compoundHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 66576762HCID 66576762, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 5-(2-hydroxypropan-2-yl)-1H-pyrazole-3-carboxylic acid (0.646 mmol, 110 mg) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.539 mmol, 140 mg) using DMF (2 ml) as the solvent. Water was added and the mixture was extracted three times with DCM. The combined organics were washed twice with water. The separated organic phase was evaporated and the residue was purified by flash chromatography and preparative HPLC, respectively. 44.6 mg of the title compound was obtained. 1H-NMR (400 MHz; DMSO-d6): δ 1.11 (d, 3H), 1.45 (s, 6H), 4.22-4.52 (m, 3H), 5.31 (s, 1H), 6.37 (s, 1H), 6.94 (d, 1H), 7.81 (d, 1H), 7.88-8.03 (m, 2H), 8.09 (s, 1H), 8.16 (d, 1H), 12.96 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. extractionthe mixture was extracted three times with DCM
  3. washThe combined organics were washed twice with water
  4. customThe separated organic phase was evaporated
  5. customthe residue was purified by flash chromatography and preparative HPLC

Sources & evidence

ORD record
ord-a11a0a01c4c74f2d9a0603ae44682347
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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