1-cyclopropyl-1H-pyrazole-3-carboxylic acid → HCID 66576846, compound

HRID 1409421Notes

Reaction equation

HRID 1409421 reaction equation
[CH:1]1([N:4]2[CH:8]=[CH:7][C:6]([C:9]([OH:11])=O)=[N:5]2)[CH2:3][CH2:2]1.[NH2:12][C@@H:13]([CH3:29])[CH2:14][N:15]1[CH:19]=[CH:18][C:17]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([Cl:28])[CH:21]=2)=[N:16]1>>[Cl:28][C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][N:15]([CH2:14][C@@H:13]([NH:12][C:9]([C:6]3[CH:7]=[CH:8][N:4]([CH:1]4[CH2:2][CH2:3]4)[N:5]=3)=[O:11])[CH3:29])[N:16]=2)[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]

Participants

3

Reactant 2

HCID 670305061-cyclopropyl-1H-pyrazole-3-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 66576846HCID 66576846, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 1-cyclopropyl-1H-pyrazole-3-carboxylic acid (0.300 g, 1.8 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-benzonitrile (0.471 g, 1.8 mmol). The product was purified by flash-chromatography. Yield: 400 mg. 1H-NMR (400 MHz; DMSO-d6): δ 0.98-1.11 (m, 7H), 3.75-3.80 (m, 1H), 4.25-4.48 (m, 3H), 6.54 (d, 1H), 6.96 (d, 1H), 7.82 (d, 2H), 7.93-7.99 (m, 2H), 8.07 (s, 1H), 8.16 (d, 1H), LC-MS: [M+1]=395.15.

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-1d7191f0f8ef4b878bbd8a1fe83ad36e
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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