4-Fluorobenzylamine → HCID 59481229, compound

HRID 2067414Notes

Reaction equation

FC1C=CC(CN)=CC=1.[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36](O)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 3

HCID 673264-Fluorobenzylamine

HCID 773174-Pyridinemethanamine

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

Product 1

HCID 59481229HCID 59481229, compoundYield 49%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 4-(aminomethyl)pyridine 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 49% yield: mp 96-97° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.47 (d, J=4.8 Hz, 2H), 7.31-7.19 (m, 7H), 6.52 (t, J=5.7 Hz, 1H), 4.53 (d, J=5.7 Hz, 2H), 4.35 (s, 2H), 4.02 (t, J=7.5 Hz, 2H), 3.41 (t, J=7.5 Hz, 2H), 2.56 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.8, 157.5, 155.3, 153.7, 149.7, 147.7, 135.4, 128.9, 128.2, 128.0, 122.3, 116.7, 47.9, 42.6, 42.0, 41.6, 17.3; MS (ES+) m/z 408.3 (M+1).

Sources & evidence

ORD record: ord-de71e7b933094a2094ff9fc9535864f6
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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