Methylamine → HCID 58387942, compound

HRID 2080184Notes

Reaction equation

[NH2:1][C:2]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:12]=[CH:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:9]=1)=[O:5].[CH3:26][NH2:27]>CS(C)=O.C(N(CC)C(C)C)(C)C.[Cl-].[Na+].O>[NH2:1][C:2]1[N:24]=[C:23]([NH:27][CH3:26])[CH:22]=[CH:21][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:12]=[CH:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH:9]=1)=[O:5]

Participants

Conditions

Temperature: 135 °C

Procedure

2-Amino-6-chloro-N-(1-(3-fluoro-benzyl)-1H-pyrrol-3-ylmethyl)-nicotinamide described in Preparation Example A+-5 (50 mg, 0.14 mmol) was dissolved in a mixture solution of dimethylsulfoxide (1 mL) and N,N-diisopropylethylamine (0.5 mL), methylamine (2.0 M tetrahydrofuran solution) (1 mL, 2 mmol) was added thereto, and the solution was heated in a sealed tube for 15 hours (oil bath temperature: 135° C.). The reaction mixture was allowed to room temperature, poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate), and the title compound (7.3 mg, 0.021 mmol, 15%) was obtained.

Workup

additionwas added
customwas allowed to room temperature
extractionthe solution was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationthen concentrated
customthe obtained residue was purified by NH silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-d57e9d7632074643a7bf250f93badf33
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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