4-Fluorobenzylamine → HCID 25094873, compound

HRID 2067411Notes

Reaction equation

FC1C=CC(CN)=CC=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15].[CH2:19]([N:26]1[CH2:30][CH2:29][N:28]([C:31]2[S:32][C:33]([C:37](O)=[O:38])=[C:34]([CH3:36])[N:35]=2)[C:27]1=[O:40])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([N:26]1[CH2:30][CH2:29][N:28]([C:31]2[S:32][C:33]([C:37]([NH:15][CH2:14][C:13]3[CH:16]=[CH:17][CH:18]=[C:11]([Cl:10])[CH:12]=3)=[O:38])=[C:34]([CH3:36])[N:35]=2)[C:27]1=[O:40])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 673264-Fluorobenzylamine

HCID 77802Benzenemethanamine, 3-chloro-

HCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 25094873HCID 25094873, compoundYield 46%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 3-chlorobenzylamine to react with 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white powder in 46% yield: mp 178-179° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.33-7.19 (m, 9H), 6.10 (s, 1H), 4.51 (d, J=5.7 Hz, 2H), 4.44 (s, 2H), 4.03 (t, J=8.4 Hz, 2H), 3.43 (t, J=8.4 Hz, 2H), 2.59 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.5, 157.3, 155.3, 153.4, 140.2, 135.5, 134.5, 130.0, 128.9, 128.3, 128.0, 127.8, 127.7, 125.8, 116.9, 47.9, 43.3, 42.0, 41.6, 17.2; MS (ES+) m/z 441.0 (M+1), 443.0 (M+1).

Sources & evidence

ORD record: ord-d95eb01997e3404a8df65456ac2181af
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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