4-(3-Isocyanatophenyl)-2-methyl-1,3-thiazole → HCID 178432517, compound

HRID 2383458Notes

Reaction equation

HRID 2383458 reaction equation
FC(F)(F)C([O-])=O.[Br:8][C:9]1[C:21]2[C:20]3[CH2:19][CH2:18][NH2+:17][CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:11][N:10]=1.[N:22]([C:25]1[CH:26]=[C:27]([C:31]2[N:32]=[C:33]([CH3:36])[S:34][CH:35]=2)[CH:28]=[CH:29][CH:30]=1)=[C:23]=[O:24]>>[Br:8][C:9]1[C:21]2[C:20]3[CH2:19][CH2:18][N:17]([C:23]([NH:22][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]5[N:32]=[C:33]([CH3:36])[S:34][CH:35]=5)[CH:26]=4)=[O:24])[CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:11][N:10]=1

Participants

3

Reactant 2

HCID 49612614-(3-Isocyanatophenyl)-2-methyl-1,3-thiazoleHCID 178419490HCID 178419490, compound

Product 1

HCID 178432517HCID 178432517, compound

Procedure

The compound 1-bromo-N-(3-(2-methylthiazol-4-yl)phenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxamide was prepared using 1-bromo-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate and 4-(3-isocyanatophenyl)-2-methylthiazole as described in general procedure M and was obtained as a pale yellow solid (0.025 g, 15%). M.p.=258-261° C.; 400 MHz 1H NMR (DMSO-d6) δ: 13.96 (s, 1H), 8.87 (s, 1H), 8.42 (s, 1H), 8.05 (m, 1H), 7.82 (m, 1H), 7.56-7.48 (m, 2H), 7.32-7.26 (m, 1H), 4.79 (s, 2H), 3.85 (t, J=6 Hz, 2H), 3.39 (t, J=6 Hz, 2H), 2.71 (s, 3H); LCMS [M+H]: 468.

Sources & evidence

ORD record
ord-9e5fb8522ae5461db5bc82610f872e9b
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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