Benzylamine → HCID 59481238, compound

HRID 2067404Notes

Reaction equation

C(N)C1C=CC=CC=1.[CH2:9]1[CH2:11][CH:10]1[CH2:12][NH2:13].[CH3:14][C:15]1[N:16]=[C:17]([N:23]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=3)[C:24]2=[O:40])[S:18][C:19]=1[C:20](O)=[O:21]>>[CH:10]1([CH2:12][NH:13][C:20]([C:19]2[S:18][C:17]([N:23]3[CH2:27][CH2:26][N:25]([CH2:28][C:29]4[CH:30]=[CH:31][C:32]([O:35][C:36]([F:37])([F:38])[F:39])=[CH:33][CH:34]=4)[C:24]3=[O:40])=[N:16][C:15]=2[CH3:14])=[O:21])[CH2:11][CH2:9]1

Participants

Reactant 3

HCID 7504Benzylamine

HCID 75646Cyclopropanemethanamine

HCID 594812844-Methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 59481238HCID 59481238, compoundYield 15%

Procedure

Following the procedure as describe in Example 8, making variations as required to replace benzylamine with 2-cyclopropylmethylamine to react with 4-methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid, the title compound was obtained as a white powder in 15% yield: mp 184-186° C.; 1H NMR (300 MHz, CDCl3) δ 7.32 (d, J=8.4 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 5.70 (s, 1H), 4.48 (s, 2H), 4.08 (t, J=8.4 Hz, 2H), 3.46 (t, J=8.4 Hz, 2H), 3.24-3.20 (m, 2H), 2.58 (s, 3H), 1.03-0.92 (m, 1H), 0.55-0.44 (m, 2H), 0.29-0.27 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.3, 156.9, 155.5, 152.7, 148.9, 134.4, 129.7, 121.4, 120.4, 117.6, 47.3, 44.8, 42.0, 41.8, 17.1, 10.6, 3.5; MS (ES+) m/z 455.3 (M+1).

Sources & evidence

ORD record: ord-8ee4c31806fa45adbe8667e5767d4627
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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