(R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 67172332, compound

HRID 872641Notes

Reaction equation

HRID 872641 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([O-:8])=O)[N:3]=[C:2]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[NH2:14][C@H:15]([CH3:31])[CH2:16][N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[CH:23]=2)=[N:18]1>>[Cl:30][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][N:17]([CH2:16][C@H:15]([NH:14][C:6]([C:4]3[N:3]=[C:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[S:1][CH:5]=3)=[O:8])[CH3:31])[N:18]=2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

Participants

3

Reactant 2

HCID 67171309(R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 77520385HCID 77520385, compound

Product 1

HCID 67172332HCID 67172332, compoundYield 66.3%

Procedure

(R)-ethyl 4-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl-carbamoyl)thiazole-2-carboxylate was prepared using the method of Example 34(d) starting from 2,4-thiazoledicarboxylic acid, 2-ethyl ester (0.528 g, 2.62 mmol) and (R)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.6 g, 2.186 mmol). The product triturated diethyl ether. Yield 66.3%. 1H-NMR (400 MHz; DMSO-d6): δ 1.17 (d, 3H), 1.34 (t, 3H), 4.34 (dd, 1H), 4.39-4.47 (m, 3H), 4.47-4.56 (m, 1H), 6.94 (d, 1H), 7.83 (d, 1H), 7.95-7.96 (m, 2H), 8.02 (dd, 1H), 8.55 (s, 1H), 8.61 (d, 1H).

Workup

  1. customThe product triturated diethyl ether

Sources & evidence

ORD record
ord-429521439c764a35aac11d143083d151
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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