1-[4-(Bromomethyl)Phenyl]-1H-Pyrazole → cis-2-[(4-Chlorobenzenesulfonyl)-(4-pyrazol-1-yl-benzyl)-amino]-cycloheptanecarboxylic acid amide

HRID 7047

Reaction equation

HRID 7047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:19]([NH2:21])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[CH:33][CH:32]=[N:31]2)=[CH:26][CH:25]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([N:30]3[CH:34]=[CH:33][CH:32]=[N:31]3)=[CH:28][CH:29]=2)[C@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[C:19]([NH2:21])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27764791-[4-(Bromomethyl)Phenyl]-1H-PyrazoleHCID 69656232cis-2-(4-Chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide

Product 1

HCID 69655561cis-2-[(4-Chlorobenzenesulfonyl)-(4-pyrazol-1-yl-benzyl)-amino]-cycloheptanecarboxylic acid amideYield 18%

Procedure

The titled compound (40 mg) was prepared in 18% yield from cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide (150 mg, 0.45 mmol) and 1-(4-bromomethyl-phenyl)-1H-pyrazole according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 8.46 (s, 1 H), 7.79 (d, 2 H, J=12.0 Hz), 7.71 (m, 3 H), 7.62 (d, 2 H, J=8.0 Hz), 7.40 (d, 2 H), J=8.0 Hz), 7.33 (s br, 1 H), 6.70 (s br, 1 H), 6.54 (s, 1 H), 4.56 (AB2,2 H,Δv=16,Jab=96 Hz), 4.00 (m, 1 H), 2.78 (m, 1 H), 2.30 (m, 1 H), 1.73 (m, 2 H), 1.37 (m, 7 H); MS m/e 509.12 (M+Na)+.

Sources & evidence

ORD record
ord-b44d5fef2bba4dd9be0b0a503504bc04
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Linked notes

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