(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 86714673, compound

HRID 1409465Notes

Reaction equation

HRID 1409465 reaction equation
[CH:1]1([C:4]2[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]=2)[CH2:3][CH2:2]1.[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>>[Cl:37][C:30]1[CH:29]=[C:28]([C:25]2[CH:26]=[CH:27][N:23]([CH2:22][C@@H:21]([NH:20][C:9]([C:7]3[N:8]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[N:5]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=3)=[O:11])[CH3:38])[N:24]=2)[CH:35]=[C:34]([F:36])[C:31]=1[C:32]#[N:33]

Participants

3

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 70980857HCID 70980857, compound

Product 1

HCID 86714673HCID 86714673, compound

Procedure

The title compound was prepared using the procedure described in Example 32(e) starting from 2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid (1.41 mmol, 400 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (1.41 mmol, 395 mg). The product was purified by flash-chromatography. Yield 249 mg. 1H-NMR (400 MHz; CDCl3): δ −0.01 (s, 9H), 0.93 (t, 2H), 0.99 (d, 4H), 1.23 (d, 3H), 1.88-1.95 (m, 1H), 3.52 (t, 2H), 4.29-4.40 (m, 2H), 4.47-4.54 (m, 1H), 5.33 (s, 2H), 6.59 (d, 1H), 7.35 (d, 1H), 7.49-7.51 (m, 2H), 7.58 (d, 1H), 7.72 (s, 1H).

Workup

  1. customThe product was purified by flash-chromatography

Sources & evidence

ORD record
ord-bc7f5cad6e3c4ff387860a0e8f01ad5a
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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