Methanol → HCID 21054842, compound

HRID 2376927Notes

Reaction equation

HRID 2376927 reaction equation
[I:1][C:2]1[C:3]([O:27][C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[N:33]([C:37]([NH:39][CH3:40])=[O:38])[CH:32]=[CH:31]3)=[N:4][C:5](N(C(OC2C=CC=CC=2)=O)C(=O)OC2C=CC=CC=2)=[N:6][CH:7]=1.CO.C[NH2:44].O.[CH3:46][N:47](C)[CH:48]=[O:49]>>[CH3:40][NH:39][C:37]([N:33]1[C:34]2[C:30](=[CH:29][C:28]([O:27][C:3]3[C:2]([I:1])=[CH:7][N:6]=[C:5]([NH:44][C:48]([NH:47][CH3:46])=[O:49])[N:4]=3)=[CH:36][CH:35]=2)[CH:31]=[CH:32]1)=[O:38]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 6228DimethylformamideHCID 6329MethylamineHCID 21949225HCID 21949225, compound

Product 1

HCID 21054842HCID 21054842, compoundYield 86%

Conditions

Temperature
0 °C

Procedure

Phenyl N-(5-iodo-4-(1-methylaminocarbonyl-1H-indol-5-yloxy)pyrimidin-2-yl)-N-(phenoxycarbonyl)carbamate (597 mg, 0.919 mmol) was dissolved in dimethylformamide (3.0 ml); a 40% methanol solution of methylamine (1.0 ml) was added while stirring at 0° C.; and the reaction mixture was further stirred for 30 minutes keeping the temperature. Water (10 ml) was added to the reaction mixture after the completion of the reaction; the precipitated crystals were filtered off, washed with water, methanol and diethyl ether, and dried under warm aeration to yield the title compound as white crystals (367 mg, 0.787 mmol, 86%).

Workup

  1. stirringand the reaction mixture was further stirred for 30 minutes
  2. customafter the completion of the reaction
  3. filtrationthe precipitated crystals were filtered off
  4. washwashed with water, methanol and diethyl ether
  5. customdried
  6. temperatureunder warm aeration

Sources & evidence

ORD record
ord-0a6fdf50564640c1a5f7dec043725ec4
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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