HCID 10037793, compound → HCID 24985615, compound

HRID 1887290Notes

Reaction equation

HRID 1887290 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][NH:13][C:14]2=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:20]([NH:27][C:28]([C:30]1[S:34][C:33](Br)=[N:32][C:31]=1[CH3:36])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([NH:27][C:28]([C:30]1[S:34][C:33]([N:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][CH:17]=[CH:18][C:9]=3[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:14]2=[O:19])=[N:32][C:31]=1[CH3:36])=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 10037793HCID 10037793, compoundHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24985615HCID 24985615, compoundYield 2%

Procedure

Following the procedure as described in Example 3, making variations only as required to use 5-(benzyloxy)isoquinolin-1(2H)-one in place of 4-aminopyridin-2(1H)-one to react with N-benzyl-2-bromo-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 2% yield: mp 225-226° C.; 1H NMR (300 MHz, CD3OD) δ 7.77 (d, J=6.0 Hz, 1H), 7.41-7.25 (m, 11H), 7.10-7.08 (m, 2H), 6.99 (d, J=9.0 Hz, 1H), 4.55 (s, 2H), 4.50 (s, 2H), 2.57 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.0, 159.6, 153.5, 151.3, 136.7, 135.0, 128.3, 127.2, 126.8, 126.7, 126.6, 126.4, 125.6, 125.4, 125.3, 125.2, 124.2, 115.5, 114.3, 99.9, 41.7, 31.1, 14.1; MS (ES+) m/z 482.3 (M+1).

Sources & evidence

ORD record
ord-2ee182500eef41a19c59f1c68b7f58fb
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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