Dimethylformamide → HCID 58919238, compound

HRID 539712Notes

Reaction equation

HRID 539712 reaction equation
N(C([C:6]1[C:7]([F:27])=[C:8]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)=O)=[N+]=[N-].[CH3:28][C:29]1[N:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=1.C[N:37]([CH:39]=[O:40])C>CCOC(C)=O>[F:27][C:7]1[C:6]([NH:37][C:39]([NH:35][C:32]2[CH:33]=[N:34][C:29]([CH3:28])=[CH:30][CH:31]=2)=[O:40])=[C:25]([F:26])[CH:24]=[CH:23][C:8]=1[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2433135-Amino-2-methylpyridineHCID 58919231HCID 58919231, compound

Product 1

HCID 58919238HCID 58919238, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 4-(3-(azidocarbonyl)-2,4-difluorobenzyl)piperazine-1-carboxylate (2.52 g, nominally 5.4 mmol, 1.0 equiv) and 6-methylpyridin-3-amine (389 mg, 3.6 mmol, 0.66 equiv) in 7 mL of DMF was stirred at room temperature over 72 h, after which, the reaction mixture was diluted with EtOAc and washed repeatedly with water. After the EtOAc layer was washed with aq. satd. NaHCO3 and brine, it was dried over sodium sulfate, filtered and concentrated in vacuo. Reverse phase chromatography provided tert-butyl 4-(2,4-difluoro-3-(3-(6-methylpyridin-3-yl)ureido)benzyl)piperazine-1-carboxylate (800 mg, 32% over 4 steps). LCMS m/z (APCI)=462.2 (M+H).

Workup

  1. washwashed repeatedly with water
  2. washAfter the EtOAc layer was washed with aq. satd
  3. dry with materialNaHCO3 and brine, it was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc5e8bbb87ad4f7c9492bf784c8e82a6
Source dataset
uspto-grants-2014_10
Patent number
US08871768B2

Reaction notes

Loading…