Benzylamine → HCID 24825735, compound

HRID 2381851Notes

Reaction equation

C(N)C1C=CC=CC=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.[CH2:18]([NH:25][C:26]([C:28]1[S:32][C:31]([N:33]2[CH:37]=[C:36]([C:38](O)=[O:39])[N:35]=[N:34]2)=[N:30][C:29]=1[CH3:41])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:25][C:26]([C:28]1[S:32][C:31]([N:33]2[CH:37]=[C:36]([C:38](=[O:39])[NH:15][CH2:14][C:13]3[CH:16]=[CH:17][C:10]([F:9])=[CH:11][CH:12]=3)[N:35]=[N:34]2)=[N:30][C:29]=1[CH3:41])=[O:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 673264-Fluorobenzylamine

HCID 68492838HCID 68492838, compound

Product 1

HCID 24825735HCID 24825735, compoundYield 11%

Procedure

Following the procedure as described in Example 18, making variations as necessary to replace benzylamine with 4-fluorobenzylamine to react with 1-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-1H-1,2,3-triazole-4-carboxylic acid, the title compound was obtained as a white solid in 11% yield: mp 198-201° C. (dichloromethane/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 9.34 (t, J=6.0 Hz, 1H), 9.23 (s, 1H), 9.02 (t, J=6.0 Hz, 1H), 7.40-7.12 (m, 9H), 4.47-4.45 (m, 4H), 2.63 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 169.4, 160.1, 158.4, 157.9, 154.3, 152.4, 152.4, 143.6, 138.9, 135.4, 129.4, 129.3, 128.3, 127.3, 126.9, 125.4, 123.6, 115.1, 114.8, 42.9, 41.4, 17.1; MS (ES+) m/z 451.4 (M+1).

Sources & evidence

ORD record: ord-77e8738b1bb146a297f3077f67bf3764
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258160B2

Reaction notes

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