2-Chloro-6-methylbenzoic acid → HCID 68973588, compound

HRID 1726222Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:37][C:38]2[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:39]=2[F:45])[C:13]2[CH:18]=[CH:17][C:16]([S:19]([N:22]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[CH3:5].[Cl:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[C:48]=1[C:49](O)=[O:50]>>[Cl:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[C:48]=1[C:49]([NH:1][CH2:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH2:37][C:38]2[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:39]=2[F:45])[C:13]2[CH:18]=[CH:17][C:16]([S:19](=[O:20])(=[O:21])[N:22]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[CH3:5])=[O:50]

Participants

Reactant 2

HCID 888702-Chloro-6-methylbenzoic acid

HCID 68970989HCID 68970989, compound

Product 1

HCID 68973588HCID 68973588, compoundYield 100%

Procedure

Using general procedure E, 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(5-chloro-2-fluoro-benzyl)-amino]-N,N-dibenzyl-benzenesulfonamide (see EXAMPLE 209) (339 mg, 0.52 mmol) and 2-chloro-6-methylbenzoic acid (116 mg, 0.68 mmol) afforded 2-chloro-N-(3-{4-[(5-chloro-2-fluoro-benzyl)-(4-dibenzylsulfamoyl-phenyl)-amino]-piperidin-1-yl}-butyl)-6-methyl-benzamide as a yellow oil (387 mg, 100%).

Sources & evidence

ORD record: ord-086ccf88f1f74302a051dd6557c058f9
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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