4-[4-Amino-5-(2,6-difluoro-benzoyl)-thiazol-2-ylamino]-benzoic Acid → 4-[4-Amino-5-(2,6-difluoro-benzoyl)-thiazol-2-ylamino]-N-(1-methyl-azetidin-3-ylmethyl)-benzamide

HRID 2085472Notes

Reaction equation

HRID 2085472 reaction equation
C(O[C:6]([N:8]1[CH2:11][CH:10]([C:12](=O)[NH2:13])[CH2:9]1)=O)(C)(C)C.[NH2:15][C:16]1[N:17]=[C:18]([NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=2)[S:19][C:20]=1[C:21](=[O:30])[C:22]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=1[F:29]>>[NH2:15][C:16]1[N:17]=[C:18]([NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36]([NH:13][CH2:12][CH:10]3[CH2:9][N:8]([CH3:6])[CH2:11]3)=[O:37])=[CH:34][CH:33]=2)[S:19][C:20]=1[C:21](=[O:30])[C:22]1[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=1[F:29]

Participants

3

Reactant 2

HCID 112573524-[4-Amino-5-(2,6-difluoro-benzoyl)-thiazol-2-ylamino]-benzoic AcidHCID 21307329tert-Butyl 3-carbamoylazetidine-1-carboxylate

Product 1

HCID 213072764-[4-Amino-5-(2,6-difluoro-benzoyl)-thiazol-2-ylamino]-N-(1-methyl-azetidin-3-ylmethyl)-benzamide

Procedure

The title compound was prepared from 3-carbamoyl-azetidine-1-carboxylic acid tert-butyl ester after 1) reduction in a manner similar to similar to Step 2 in Example A39 and 2) subsequent coupling with 4-[4-amino-5-(2,6-difluoro-benzoyl)-thiazol-2-ylamino]-benzoic acid (3) in a manner similar to Step 3 in Method A.

Sources & evidence

ORD record
ord-f599393720834a379ddd97fd356af7df
Source dataset
uspto-grants-2004_04
Patent number
US06720346B2

Reaction notes

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