5-Methylthiophene-2-carboxylic acid → 5-Methyl-thiophene-2-carboxylic acid (7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-amide

HRID 2222143Notes

Reaction equation

HRID 2222143 reaction equation
[O:1]1[CH2:7][CH:6]([C:8]2[C:16]3[S:15][C:14]([NH2:17])=[N:13][C:12]=3[C:11]([O:18][CH3:19])=[CH:10][CH:9]=2)[CH2:5][O:4][CH2:3][CH2:2]1.[CH3:20][C:21]1[S:25][C:24]([C:26](O)=[O:27])=[CH:23][CH:22]=1.COC1C2N=C(NC(=O)C3C=CC=CC=3)SC=2C(C2C=CC=CC=2)=CC=1>>[O:4]1[CH2:5][CH:6]([C:8]2[C:16]3[S:15][C:14]([NH:17][C:26]([C:24]4[S:25][C:21]([CH3:20])=[CH:22][CH:23]=4)=[O:27])=[N:13][C:12]=3[C:11]([O:18][CH3:19])=[CH:10][CH:9]=2)[CH2:7][O:1][CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 747135-Methylthiophene-2-carboxylic acidHCID 22283378N-(4-Methoxy-7-phenyl-benzothiazol-2-yl)-benzamideHCID 597118057-[1,4]Dioxepan-6-yl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 113731005-Methyl-thiophene-2-carboxylic acid (7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-amide

Procedure

7-[1,4]Dioxepan-6-yl-4-methoxy-benzothiazol-2-ylamine and 5-methyl-thiophene-2-carboxylic acid were reacted as described for N-(4-methoxy-7-phenyl-benzothiazol-2-yl)-benzamide in WO01/9786. Usual workup, preparative reversed-phase HPLC and final dry-freezing afforded the title compound as white powder. MS: m/e=405(M+H+). Following the general method of example 1 the compounds of examples 9 to 16 were prepared.

Workup

  1. customUsual workup, preparative reversed-phase HPLC and final dry-freezing

Sources & evidence

ORD record
ord-afb64026dd9e454e99b5efb9fc96644e
Source dataset
uspto-grants-2008_05
Patent number
US07371748B2

Reaction notes

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