(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 86714668, compound

HRID 1409457Notes

Reaction equation

HRID 1409457 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:4]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=[C:6]([C:8]([OH:10])=O)[N:7]=1.[NH2:21][C@@H:22]([CH3:39])[CH2:23][N:24]1[CH:28]=[CH:27][C:26]([C:29]2[CH:36]=[C:35]([F:37])[C:32]([C:33]#[N:34])=[C:31]([Cl:38])[CH:30]=2)=[N:25]1>>[Cl:38][C:31]1[CH:30]=[C:29]([C:26]2[CH:27]=[CH:28][N:24]([CH2:23][C@@H:22]([NH:21][C:8]([C:6]3[N:7]=[C:3]([C:2]([F:1])([F:20])[F:19])[N:4]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=3)=[O:10])[CH3:39])[N:25]=2)[CH:36]=[C:35]([F:37])[C:32]=1[C:33]#[N:34]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70981461HCID 70981461, compound

Product 1

HCID 86714668HCID 86714668, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 2-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (0.97 mmol, 300 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.97 mmol, 269 mg). The product was purified by flash-chromatography. Yield 230 mg. 1H-NMR (400 MHz; DMSO-d6): δ −0.13 (s, 9H), 0.65-0.77 (m, 2H), 1.17 (d, 3H), 3.36-3.43 (m, 2H), 4.21-4.42 (m, 3H), 5.75 (q, 2H), 7.01 (s, 1H), 7.64 (s, 1H), 7.83-7.88 (m, 2H), 7.95 (s, 1H), 8.65 (d, 1H). LC-MS: [M+1]=571.01.

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-2010590a2c004e818bb10485450dd3c7
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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