(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 70656310, compound

HRID 872621Notes

Reaction equation

HRID 872621 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.[N:19]1([CH2:24][C:25]2[S:29][C:28]([C:30](O)=[O:31])=[N:27][CH:26]=2)[CH:23]=[CH:22][N:21]=[CH:20]1>>[N:19]1([CH2:24][C:25]2[S:29][C:28]([C:30]([NH:1][C@@H:2]([CH3:18])[CH2:3][N:4]3[CH:8]=[CH:7][C:6]([C:9]4[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:17])[CH:10]=4)=[N:5]3)=[O:31])=[N:27][CH:26]=2)[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

3

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 67172452HCID 67172452, compound

Product 1

HCID 70656310HCID 70656310, compoundYield 5%

Procedure

(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (157 mg, 0.60 mmol) was coupled with 5-((1H-imidazol-1-yl)methyl)thiazole-2-carboxylic acid (0.60 mmol) using the method of Example 34(d). Crude product was purified twice by CombiFlash (1st column: C-18, eluent: 0-100% MeCN in water; 2nd column: silica, eluent: 0-8% MeOH in DCM) to yield 13 mg (5%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.18 (d, 2H), 4.29-4.52 (m, 3H), 5.36 (s, 2H), 6.92 (s, 1H), 6.94 (dd, 1H), 7.22 (s, 1H), 7.71 (s, 1H), 7.75 (s, 1H), 7.83 (d, 1H), 7.90 (dd, 1H), 7.96 (d, 1H), 8.04 (d, 1H), 8.83 (d, 1H).

Workup

  1. customCrude product was purified twice by CombiFlash (1st column: C-18, eluent: 0-100% MeCN in water; 2nd column: silica, eluent: 0-8% MeOH in DCM)

Sources & evidence

ORD record
ord-78931459b69b4c8bb6424f30bc7aca17
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…