Benzylamine → HCID 24958969, compound

HRID 2381852Notes

Reaction equation

HRID 2381852 reaction equation
[CH2:1]([NH:8]C(C1SC(N2C=C(C(O)=O)N=N2)=NC=1C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([NH:32][C:33]([C:35]1[S:39][C:38]([N:40]2[C:44]([CH3:45])=[C:43]([C:46]([OH:48])=O)[N:42]=[N:41]2)=[N:37][C:36]=1[CH3:49])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N)C1C=CC=CC=1>>[CH2:25]([NH:32][C:33]([C:35]1[S:39][C:38]([N:40]2[C:44]([CH3:45])=[C:43]([C:46](=[O:48])[NH:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:42]=[N:41]2)=[N:37][C:36]=1[CH3:49])=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 68492838HCID 68492838, compoundHCID 68492935HCID 68492935, compound

Product 1

HCID 24958969HCID 24958969, compoundYield 11%

Procedure

Following the procedure as described in Example 18, making variations as necessary to replace 1-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-1H-1,2,3-triazole-4-carboxylic acid with 1-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid to react with benzylamine, the title compound was obtained as a white solid in 11% yield (0.033 g): mp 183-186° C. (methanol); 1H NMR (300 MHz, DMSO-d6) δ 9.30 (t, J=6.0 Hz, 1H), 9.01 (t, J=6.0 Hz, 1H), 7.36-7.22 (m, 10H), 4.46 (d, J=6.0 Hz, 4H), 2.90 (s, 3H), 2.64 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 160.1, 159.9, 155.1, 152.4, 139.4, 139.2, 138.9, 137.5, 128.3, 128.2, 127.3, 127.2, 126.9, 126.7, 125.1, 42.8, 41.9, 17.2, 10.3; MS (ES+) m/z 447.4 (M+1).

Sources & evidence

ORD record
ord-a1ba8eedf5544709a1d08349afb1096a
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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