Benzylamine → HCID 24955065, compound

HRID 1879172Notes

Reaction equation

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

Participants

Reactant 3

HCID 7504Benzylamine

HCID 75646Cyclopropanemethanamine

HCID 68492747HCID 68492747, compound

Product 1

HCID 24955065HCID 24955065, compoundYield 75%

Procedure

Following the procedure described in Example 1 (Part A), making variations as required to replace benzylamine with cyclopropane-methyl-amine to react with 2-{6-[(4-fluoro-benzyl)-methyl-amino]-pyrazin-2-yl}-4-methyl-thiazole-5-carboxylic acid, the title compound was obtained in 75% yield. 1H NMR (400 MHz, CD2Cl2) δ 8.58 (s, 1H), 8.05 (s, 1H), 7.25-7.31 (m, 2H), 6.98-7.05 (m, 2H), 5.95 (bs, 1H), 4.82 (s, 2H), 3.21-3.26 (m, 2H), 3.15 (s, 3H), 2.70 (s, 3H), 1.00-1.10 (m, 1H), 0.50-0.57 (m, 2H), 0.22-0.28 (m, 2H); MS (ES+) m/z 412.3 (M+1), Rt=1.52 min.

Sources & evidence

ORD record: ord-08d206a00c7c4b0699667be4fce1100b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314138B2

Reaction notes

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