(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 66576923, compound

HRID 1409436Notes

Reaction equation

HRID 1409436 reaction equation
[NH2:1][C@@H:2]([CH3:18])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=2)=[N:5]1.[CH2:19]([C:23]1[N:24]([CH3:32])[CH:25]=[C:26]([C:28](OC)=[O:29])[N:27]=1)[CH2:20][CH2:21][CH3:22]>>[CH2:19]([C:23]1[N:24]([CH3:32])[CH:25]=[C:26]([C:28]([NH:1][C@@H:2]([CH3:18])[CH2:3][N:4]2[CH:8]=[CH:7][C:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=3)=[N:5]2)=[O:29])[N:27]=1)[CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 86714662HCID 86714662, compound

Product 1

HCID 66576923HCID 66576923, compound

Procedure

The title compound was prepared using the procedure described in Example 52(g) starting from (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzo-nitrile (664 mg, 2.55 mmol) and methyl 2-butyl-1-methyl-1H-imidazole-4-carboxylate (500 mg, 2.55 mmol). The product was purified with flash chromatography. Yield 291 mg. 1H-NMR (400 MHz; DMSO-d6): δ 0.88 (t, 3H), 1.09 (t, 3H), 1.28-1.36 (m, 2H), 1.54-1.61 (m, 2H), 2.62 (t, 2H), 3.57 (s, 3H), 4.26-4.39 (m, 3H), 6.95 (bs, 1H), 7.47 (s, 1H), 7.82 (d, 1H), 7.90 (d, 1H), 7.96 (s, 2H), 8.09 (s, 1H).

Workup

  1. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-5246a5b354a8495c8433204fd57870c4
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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