Methylamine → HCID 86681022, compound

HRID 1847998Notes

Reaction equation

[CH3:1][NH2:2].C[Al](C)C.[CH3:7][S:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([CH2:18][N:19]3[CH:23]=[C:22]([C:24]([O-:26])=O)[N:21]=[CH:20]3)[CH:15]=[CH:14][C:12]=2[N:13]=1>C1COCC1.C1(C)C=CC=CC=1.ClCCCl>[CH3:1][NH:2][C:24]([C:22]1[N:21]=[CH:20][N:19]([CH2:18][C:16]2[CH:15]=[CH:14][C:12]3[N:13]=[C:9]([S:8][CH3:7])[S:10][C:11]=3[CH:17]=2)[CH:23]=1)=[O:26]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of methylamine (623 μL of a 2 M solution in THF, 1.3 mmol) at 0° C. was added trimethylaluminum (623 μL of a 2 M solution in toluene, 1.2 mmol). The mixture was stirred for 2 min and then a solution of 1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-1H-imidazole-4-carboxylate (80 mg, 0.25 mmol) from Step 1 of this Example in DCE (1 mL) was added dropwise. The reaction vessel was sealed and the mixture was heated at 70° C. for 20 h. The mixture was then concentrated under reduced pressure and the residue was purified by silica gel flash chromatography eluting with 5% MeOH in EtOAc to afford N-methyl-1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-1H-imidazole-4-carboxamide (46 mg, 58%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.98 (d, J=1.3 Hz, 1H), 7.81-7.94 (m, 3H), 7.71 (d, J=1.1 Hz, 1H), 7.42 (dd, J=1.6, 8.4 Hz, 1H), 5.33 (s, 2H), 2.78 (s, 3H), 2.70 (d, J=4.9 Hz, 3H). LCMS (ESI) m/z 319 (M+H)+.

Workup

customThe reaction vessel was sealed
concentrationThe mixture was then concentrated under reduced pressure
customthe residue was purified by silica gel flash chromatography
washeluting with 5% MeOH in EtOAc

Sources & evidence

ORD record: ord-a56b1bcfc8e243b2a974b1f0fd4067db
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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