1,2-Dichloroethane → 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamide

HRID 1880324Notes

Reaction equation

HRID 1880324 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[CH3:18])[C:5]([C:19]([OH:21])=O)=[CH:4][N:3]=1.[CH:22]1[CH:23]=[CH:24][C:25]2[N:30]([OH:31])[N:29]=[N:28][C:26]=2[CH:27]=1.C(Cl)CCl.[NH3:36]>CN(C=O)C.CCOC(C)=O.O>[N:30]1([O:31][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:10]=3[CH:11]=[CH:12][N:13]4[CH3:18])[C:5]([C:19]([NH2:36])=[O:21])=[CH:4][N:3]=2)[C:25]2[CH:24]=[CH:23][CH:22]=[CH:27][C:26]=2[N:28]=[N:29]1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 574720122-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acid

Product 1

HCID 574720132-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamideYield 87.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acid (325 mg, 1.08 mmol) and HOBt (198 mg, 1.29 mmol) in DMF (4 mL), EDC (248 mg, 1.29 mmol) was added. The mixture was stirred at room temperature for 1.5 h. Ammonia (0.5 M in dioxane, 8.00 mL, and 4.00 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-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamide (378 mg). MS 401.4 (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-301cd7dab63c4959987de8ec91be12df
Source dataset
uspto-grants-2012_11
Patent number
US08318755B2

Reaction notes

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