N'-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine → Cyc-116

HRID 599136Notes

Reaction equation

HRID 599136 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:11][C:10]([N:12]=CN(C)C)=[N:9][C:8]=1[CH3:17])=O.[N+]([O-])(O)=O.[N:23]1([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH2:38])=[NH:37])=[CH:31][CH:30]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>>[NH2:12][C:10]1[S:11][C:7]([C:5]2[CH:4]=[CH:3][N:38]=[C:36]([NH:35][C:32]3[CH:31]=[CH:30][C:29]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:34][CH:33]=3)[N:37]=2)=[C:8]([CH3:17])[N:9]=1

Participants

3

Reactant 2

HCID 67218485N'-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidineHCID 178512568N-(4-morpholin-4-yl-phenyl)-guanidine nitrate

Product 1

HCID 6420138Cyc-116

Procedure

By condensation between N′-[5-(3-dimethylamino-acryloyl)-4-methyl-thiazol-2-yl]-N,N-dimethyl-formamidine (prepared from 1-(2-amino-4-methyl-thiazol-5-yl)-ethanone and N,N-dimethylformamide dimethylacetal) and N-(4-morpholin-4-yl-phenyl)-guanidine nitrate. Yellow solid. M.p. 300-304° C.: 1H-NMR (DMSO-d6) δ: 2.46 (s, 3H, CH3), 3.07 (m, 4H, CH2), 3.76 (m, 4H, CH2), 6.85 (d, 1H, J=5.3 Hz, pyrimidinyl-H), 6.92 (m, 2H, Ph-H), 7.53 (br. s, 1H, NH), 7.67 (m, 2H, Ph-H), 8.30 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 9.25 (br. s, 1H, NH). MS (ESI+) m/z 369 [M+H]+ (C18H20N6OS requires 368.5).

Sources & evidence

ORD record
ord-b6622778d7cb4f3ca3ff166fd0bf2d53
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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