Cyclopropanemethanamine → HCID 59179634, compound

HRID 883167Notes

Reaction equation

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

Participants

Reactant 2

HCID 75646Cyclopropanemethanamine

HCID 24799235HCID 24799235, compound

Product 1

HCID 59179634HCID 59179634, compoundYield 69%

Procedure

Following the procedure as described in Example 5, making variation as required to use cyclopropylmethanamine in place of 2-cyclopropylethanamine to react with N-benzyl-2-(3-bromo-2-oxopiperidin-1-yl)-4-methylthiazole-5-carboxamide in place of 2-(3-bromo-2-oxopyrrolidin-1-yl)-N-(4-fluorobenzyl)-4-methylthiazole-5-carboxamide, the title compound was obtained as a white solid in 69% yield: mp 125-126° C. (diethyl ether); 1H NMR (300 MHz, CDCl3) δ 7.38-7.29 (m, 5H), 5.95 (t, J=5.5 Hz, 1H), 4.56 (d, J=5.5 Hz, 2H), 4.37-4.26 (m, 1H), 4.04-3.91 (m, 1H), 3.54-3.45 (m, 1H), 2.63 (s, 3H), 2.59-2.44 (m, 2H), 2.31-1.82 (m, 4H), 1.81-1.68 (m, 1H), 1.01-0.89 (m, 1H), 0.57-0.41 (m, 2H), 0.23-0.08 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 171.5, 162.5, 156.7, 152.2, 137.9, 128.8, 127.9, 127.7, 119.6, 58.5, 52.5, 47.6, 44.1, 26.4, 20.5, 17.4, 11.2, 3.6, 3.3; MS (ES+) m/z 399.3 (M+1).

Sources & evidence

ORD record: ord-a40b167cd86441339abce78f3dd68b93
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236835B2

Reaction notes

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