Benzylamine → HCID 59369698, compound

HRID 45368Notes

Reaction equation

[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([NH:17][C:18]1[S:19][C:20]([C:24](O)=[O:25])=[C:21]([Cl:23])[N:22]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:1]([NH:8][C:24]([C:20]1[S:19][C:18]([NH:17][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:22][C:21]=1[Cl:23])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 866425162-Benzoylamino-4-chlorothiazole-5-carboxylic Acid

Product 1

HCID 59369698HCID 59369698, compoundYield 20%

Procedure

Following the procedure as described in Example 3, making variations only as required to use benzylamine in place of α-ethylbenzylamine to react with 2-benzoylamino-4-chlorothiazole-5-carboxylic acid, the title compound was obtained as a white solid in 20% yield; m. p. 247-249° C.; 1H NMR (DMSO-d6, 300 MHz) δ 12.5 (s, 1H), 8.11-7.93 (m, 2H), 7.72 (t, J=5.7 Hz, 1H), 7.58-6.95 (m, 8H), 4.48 (d, J=5.7 Hz, 2H); 13C NMR (DMSO-d6, 75 MHz) δ 166.1, 160.0, 138.5, 134.2, 133.0, 131.4, 128.6, 128.5, 128.4, 127.5, 127.2, 119.6, 43.4; MS (ES+) m/z 372.3 (M+1).

Sources & evidence

ORD record: ord-08a2d1c3f0dd4a4bb2c352f261f8bd8f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Reaction notes

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