Dimethylformamide → HCID 23153485, compound

HRID 492863Notes

Reaction equation

HRID 492863 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6]C(NC)[CH2:4][CH2:3]1.[CH2:10]([O:17][C:18]([NH:20][C:21]1[CH:52]=[CH:51][C:24]([O:25][C:26]2[N:31]=[CH:30][N:29]=[C:28]([N:32](C(OC3C=CC=CC=3)=O)C(=O)OC3C=CC=CC=3)[CH:27]=2)=[CH:23][C:22]=1[F:53])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:54][N:55]([CH3:58])[CH:56]=[O:57]>>[F:53][C:22]1[CH:23]=[C:24]([O:25][C:26]2[CH:27]=[C:28]([NH:32][C:56]([N:55]([CH3:58])[CH:54]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[O:57])[N:29]=[CH:30][N:31]=2)[CH:51]=[CH:52][C:21]=1[NH:20][C:18](=[O:19])[O:17][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 5663231-Methyl-4-(methylamino)piperidineHCID 23153549HCID 23153549, compound

Product 1

HCID 23153485HCID 23153485, compound

Procedure

After adding a solution of 1-methyl-4-methylaminopiperidine (0.355 ml) in N,N-dimethylformamide (2.5 ml) to crude phenyl N-[6-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyrimidin-4-yl]-N-(phenoxycarbonyl)carbamate (358 mg) at room temperature, the mixture was stirred for 2 hours. The reaction mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with 1N aqueous sodium hydroxide and brine in that order and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate, then ethyl acetate:methanol=95:5) to provide the title compound (189.4 mg) as white powder.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe separated organic layer was washed with 1N aqueous sodium hydroxide and brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent

Sources & evidence

ORD record
ord-9f7a0f0b4f424ddea2a36576789d5307
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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