1,2-Dichloroethane → 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxamide

HRID 559009Notes

Reaction equation

HRID 559009 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[C:11]([F:20])[CH:10]=2)[C:5]([C:21]([OH:23])=O)=[CH:4][N:3]=1.[CH:24]1[CH:25]=[CH:26][C:27]2[N:32]([OH:33])[N:31]=[N:30][C:28]=2[CH:29]=1.C(Cl)CCl.[NH3:38]>CN(C=O)C.CCOC(C)=O.O>[N:32]1([O:33][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH:19]=[CH:18][N:17]=[CH:16]4)=[C:11]([F:20])[CH:10]=3)[C:5]([C:21]([NH2:38])=[O:23])=[CH:4][N:3]=2)[C:27]2[CH:26]=[CH:25][CH:24]=[CH:29][C:28]=2[N:30]=[N:31]1

Participants

8

Reactant 4

HCID 111,2-Dichloroethane2×HCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 574718862-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid

Product 1

HCID 574718872-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxamideYield 66.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid (68 mg, 0.20 mmol) and HOBt (63 mg, 0.41 mmol) in DMF (2 mL), EDC (60 mg, 0.31 mmol) was added. The mixture was stirred at room temperature for 1.5 h. Ammonia (0.5 M in dioxane, 0.800 mL, 0.40 mmol) was added. It was stirred at room temperature overnight. More EDC (100 mg, 0.52 mmol) was added. It was stirred for another 24 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-imidazol-1-yl)phenylamino)pyrimidine-5-carboxamide (57 mg). MS 432.2 (M+H)

Workup

  1. stirringIt was stirred at room temperature overnight
  2. stirringIt was stirred for another 24 h
  3. customThe organic phase was separated
  4. washwashed with 5% NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-196e35a658214150a0c561bcef926300
Source dataset
uspto-grants-2011_11
Patent number
US08063058B2

Reaction notes

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