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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1846748Generated: November 2, 2026

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

https://huagongshe.com/reaction/1846748

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
ReactantAmmoniaHCID 222—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant2-chloro-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxylic acidHCID 57472012—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(1-methyl-1H-indol-4-ylamino)pyrimidine-5-carboxamideHCID 5747201387.4%

Reaction Steps

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)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952027B2
Source datasetuspto-grants-2015_02
ORD IDord-e5c905b2ccc64caaa0cadfc23cf0ac90
Source noteuspto-grants-2015_02