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

HRID 1802002Notes

Reaction equation

HRID 1802002 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][CH:17]=[N: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][CH:17]=[N: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-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 57471876HCID 57471876, compound

Product 1

HCID 574718772-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxamideYield 61.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-4-(3-fluoro-4-(1H-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxylic acid (230 mg, 0.690 mmol) and HOBt (158 mg, 1.03 mmol) in DMF (4 mL), EDC (200 mg, 1.04 mmol) was added. The mixture was stirred at room temperature for 1.5 h. Ammonia (0.5 M in dioxane, 6.00 mL, 3.00 mmol) was added. It was stirred at room temperature overnight. Water and EtOAc were added. The organic phase was separated, washed with 1 N HCl, then 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-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxamide (184 mg). MS 432.4 (M+H)

Workup

  1. stirringIt was stirred at room temperature overnight
  2. customThe organic phase was separated
  3. washwashed with 1 N HCl
  4. dry with materialwith 5% NaHCO3, dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-983e2c14e60f470c8d2f1dcda9b19c02
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

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