(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 70656401, compound

HRID 872656Notes

Reaction equation

HRID 872656 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[S:10][CH:11]=[C:12]([C:14]([OH:16])=O)[N:13]=2)[CH2:4][CH2:3]1.[NH2:17][C@@H:18]([CH3:34])[CH2:19][N:20]1[CH:24]=[CH:23][C:22]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([Cl:33])[CH:26]=2)=[N:21]1>>[Cl:33][C:27]1[CH:26]=[C:25]([C:22]2[CH:23]=[CH:24][N:20]([CH2:19][C@@H:18]([NH:17][C:14]([C:12]3[N:13]=[C:9]([CH2:8][N:5]4[CH2:4][CH2:3][O:2][CH2:7][CH2:6]4)[S:10][CH:11]=3)=[O:16])[CH3:34])[N:21]=2)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 70656016HCID 70656016, compound

Product 1

HCID 70656401HCID 70656401, compoundYield 68.7%

Procedure

(S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(morpholinomethyl)thiazole-4-carboxamide was prepared using the method of Example 34(d) starting from 2-(morpholinomethyl)thiazole-4-carboxylic acid hydrochloride (260 mg, 0.982 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (218 mg, 0.818 mmol). The product was purified by washing the organic phase with 1M HCl, 1M Na2CO3, brine and water. Yield 68.7%. 1H-NMR (400 MHz; DMSO-d6): δ 1.23 (d, 3H), 2.50 (t, 4H; overlap with DMSO), 3.61 (t, 4H), 3.85 (d, 2H), 4.32 (dd, 1H), 4.40 (dd, 1H), 4.43-4.50 (m, 1H), 6.96 (d, 1H), 7.84 (d, 1H), 7.95 (dd, 1H), 7.98 (dd, 1H), 8.02 (dd, 1H), 8.16 (s, 1H), 8.46 (d, 1H). m/z [471.0+1].

Workup

  1. customThe product was purified
  2. washby washing the organic phase with 1M HCl, 1M Na2CO3, brine and water

Sources & evidence

ORD record
ord-02779ef7550b4696b19bf7e60e54513e
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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