Benzylamine → HCID 24955414, compound

HRID 1879169Notes

Reaction equation

HRID 1879169 reaction equation
C(N)C1C=CC=CC=1.[NH2:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[F:17][C:18]1[CH:43]=[CH:42][C:21]([O:22][CH2:23][CH2:24][N:25]([CH3:41])[C:26]2[N:31]=[C:30]([C:32]3[S:33][C:34]([C:38](O)=[O:39])=[C:35]([CH3:37])[N:36]=3)[CH:29]=[N:28][CH:27]=2)=[CH:20][CH:19]=1>>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][NH:9][C:38]([C:34]2[S:33][C:32]([C:30]3[CH:29]=[N:28][CH:27]=[C:26]([N:25]([CH2:24][CH2:23][O:22][C:21]4[CH:20]=[CH:19][C:18]([F:17])=[CH:43][CH:42]=4)[CH3:41])[N:31]=3)=[N:36][C:35]=2[CH3:37])=[O:39])[CH:12]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 310183-PyridinemethanamineHCID 68491522HCID 68491522, compound

Product 1

HCID 24955414HCID 24955414, compoundYield 85%

Procedure

Following the procedure described in Example 1 (Part A), making variations as required to replace benzylamine with 3-(aminomethyl)-pyridine to react with 2-(6-{[2-(4-fluoro-phenoxy)-ethyl]-methyl-amino}-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid, the title compound was obtained in 85% yield. 1H NMR (400 MHz, CD2Cl2) δ 8.51 (s, 1H), 8.47-8.62 (m, 2H), 8.12 (s, 1H), 7.67-7.73 (m, 1H), 7.25-7.30 (m, 1H), 6.90-6.96 (m, 2H), 6.78-6.84 (m, 2H), 6.31 (bs, 1H), 4.59 (d, J=4.0 Hz, 2H), 4.16-4.21 (m, 2H), 3.95-4.01 (m, 2H), 3.23 (s, 3H), 2.70 (s, 3H); MS (ES+) m/z 479.2 (M+1), Rt=1.36 min.

Sources & evidence

ORD record
ord-068034c19af4437282b1e3db60705c95
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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