Methylamine → 3-Methyl-1-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea

HRID 2353702Notes

Reaction equation

HRID 2353702 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[C:12]([C:14]([S:17]([CH3:20])(=[O:19])=[O:18])([CH3:16])[CH3:15])[N:11]=[C:10]([C:21]2[S:25][C:24]([NH:26][C:27](=O)[O:28]C3C=CC=CC=3)=[N:23][CH:22]=2)[N:9]=1.CN.[CH2:38]([N:40](CC)CC)C>CN1C(=O)CCC1>[CH3:38][NH:40][C:27](=[O:28])[NH:26][C:24]1[S:25][C:21]([C:10]2[N:9]=[C:8]([N:3]3[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]3[CH3:1])[CH:13]=[C:12]([C:14]([S:17]([CH3:20])(=[O:19])=[O:18])([CH3:16])[CH3:15])[N:11]=2)=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 59380099phenyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]carbamate

Product 1

HCID 593800023-Methyl-1-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of phenyl N-[5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]carbamate (200 mg, 0.39 mmol), methyl amine (1.5 mmol) and triethylamine (0.163 mL, 1.16 mmol) in NMP (3 mL) was heated at 70° C. for 2 hours. The mixture was chromatographed on silica, eluting with 0-5% methanol in ethyl acetate to give the desired material.

Workup

  1. customThe mixture was chromatographed on silica
  2. washeluting with 0-5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-054abc9504b14d2db283e52a490366f0
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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