4-Fluorobenzylamine → HCID 24985445, compound

HRID 1887262Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH:10]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N:19]([C:22]3[S:23][C:24]([C:28](O)=[O:29])=[C:25]([CH3:27])[N:26]=3)[C:18](=[O:31])[CH:17]=2)[CH2:12][CH2:11]1>>[CH:10]1([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][N:19]([C:22]3[S:23][C:24]([C:28]([NH:7][CH2:6][C:5]4[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=4)=[O:29])=[C:25]([CH3:27])[N:26]=3)[C:18](=[O:31])[CH:17]=2)[CH2:12][CH2:11]1

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 24986107HCID 24986107, compound

Product 1

HCID 24985445HCID 24985445, compoundYield 30%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 4-fluorobenzylamine in place of benzylamine to react with 2-(4-(2-cyclopropylethoxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 30% yield: mp 172-174° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.64 (d, J=8.1 Hz, 1H), 8.32-8.27 (m, 2H), 7.05-7.00 (m, 2H), 6.17-6.08 (m, 2H), 5.97 (t, J=2.5 Hz, 1H), 4.54 (d, J=5.7 Hz, 2H), 4.03 (t, J=6.6 Hz, 2H), 2.67 (s, 3H), 1.68 (q, J=6.6 Hz, 2H), 0.87-0.93 (m, 1H), 0.54-0.46 (m, 2H), 0.13-0.08 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 167.9, 163.9, 162.2, 160.6, 153.6, 152.4, 133.6, 131.3, 129.6, 122.0, 115.8, 104.2, 96.6, 69.1, 43.3, 33.6, 17.3, 7.5, 4.2; MS (ES+) m/z 428.2 (M+1).

Sources & evidence

ORD record: ord-df0f6225944142afa9c605a5d5292806
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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