(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 70981912, compound

HRID 1409392Notes

Reaction equation

HRID 1409392 reaction equation
[C:1]([C:4]1[N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[C:7]([C:9]([OH:11])=O)[N:8]=1)(=[O:3])[CH3:2].[NH2:20][C@@H:21]([CH3:38])[CH2:22][N:23]1[CH:27]=[CH:26][C:25]([C:28]2[CH:35]=[C:34]([F:36])[C:31]([C:32]#[N:33])=[C:30]([Cl:37])[CH:29]=2)=[N:24]1>>[C:1]([C:4]1[N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[C:7]([C:9]([NH:20][C@@H:21]([CH3:38])[CH2:22][N:23]2[CH:27]=[CH:26][C:25]([C:28]3[CH:35]=[C:34]([F:36])[C:31]([C:32]#[N:33])=[C:30]([Cl:37])[CH:29]=3)=[N:24]2)=[O:11])[N:8]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70980194HCID 70980194, compound

Product 1

HCID 70981912HCID 70981912, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 2-acetyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (400 mg, 1.4 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (389 mg, 1.4 mmol). The product was purified with flash chromatography. Yield 260 mg. 1H-NMR (400 MHz; DMSO-d6): δ −0.09 (s, 9H), 0.81 (t, 2H), 1.15 (d, 3H), 2.61 (s, 3H), 3.48 (t, 2H), 4.33-4.48 (m, 3H), 5.66 (s, 2H), 7.02 (d, 1H), 7.84-7.87 (m, 2H), 7.95 (s, 1H), 8.06 (s, 1H), 8.15 (d, 1H).

Workup

  1. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-04aa073801e04393a386dea9cc70496c
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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