3-(Morpholino)phenylboronic acid → 5-amino-N-(1-methyl-1H-pyrazol-4-yl)-2-(3-morpholinophenyl)thiazole-4-carboxamide

HRID 1185321Notes

Reaction equation

HRID 1185321 reaction equation
Br[C:2]1[S:3][C:4]([NH:16]C(=O)OC(C)(C)C)=[C:5]([C:7](=[O:15])[NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[N:6]=1.[O:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=2)[CH2:26][CH2:25]1>>[NH2:16][C:4]1[S:3][C:2]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([N:27]3[CH2:26][CH2:25][O:24][CH2:29][CH2:28]3)[CH:35]=2)=[N:6][C:5]=1[C:7]([NH:8][C:9]1[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=1)=[O:15]

Participants

3

Reactant 2

HCID 41926613-(Morpholino)phenylboronic acidHCID 67438038tert-butyl 2-bromo-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate

Product 1

HCID 584647385-amino-N-(1-methyl-1H-pyrazol-4-yl)-2-(3-morpholinophenyl)thiazole-4-carboxamideYield 59%

Procedure

Following Example 278, Suzuki coupling of (tert-butyl 2-bromo-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate and 3-morpholinophenylboronic acid gave 244 as a beige solid (56 mg, 59% over two steps). 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 7.96 (s, 1H), 7.53 (s, 1H), 7.25-6.95 (m, 4H), 6.07 (s, 2H), 3.92-3.88 (m, 7H), 3.24 (t, J=5 Hz, 4H). LCMS (ES+) m/z 385 (M+1)

Sources & evidence

ORD record
ord-082589425396460a8c441bafab62f1c4
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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