Bromomethylcyclopropane → HCID 57744458, compound

HRID 1887317Notes

Reaction equation

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

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 54742340N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

Product 1

HCID 57744458HCID 57744458, compoundYield 62%

Procedure

Following the procedure as described in Example 9, making variations only as required to use cyclopropylmethyl bromide in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide, the title compound was obtained as a colorless solid in 62% yield: mp 175-177° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.54 (t, J=6.0 Hz, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.35-7.20 (m, 6H), 6.24 (dd, J=8.0, 2.7 Hz, 1H), 5.97 (d, J=2.7 Hz, 1H), 4.41 (d, J=6.0 Hz, 2H), 3.88 (d, J=7.2 Hz, 2H), 2.42 (s, 3H), 1.27-1.14 (m, 1H), 0.63-0.54 (m, 2H), 0.37-0.29 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 166.5, 162.4, 161.0, 139.6, 138.8, 137.2, 134.9, 128.2, 127.2, 127.1, 126.6, 120.4, 102.5, 96.6, 73.1, 42.3, 15.5, 9.5, 3.1; MS (ES+) m/z 395.2 (M+1).

Sources & evidence

ORD record: ord-3674052aaf9a4e37806e4443823f51e5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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