2,2,2-Trichloroethyl chloroformate → {5-[7-(3-Methanesulfonyl-phenyl)-4-morpholin-4-yl-quinazolin-2-yl]-pyridine-2-yl}-carbamic acid 2,2,2-trichloroethyl ester

HRID 517445Notes

Reaction equation

HRID 517445 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:20]=[C:19]3[C:14]([C:15]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[N:16][C:17]([C:21]4[CH:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[Cl:34][C:35]([Cl:42])([Cl:41])[CH2:36][O:37][C:38](Cl)=[O:39]>C(Cl)Cl>[Cl:34][C:35]([Cl:42])([Cl:41])[CH2:36][O:37][C:38](=[O:39])[NH:27][C:24]1[CH:23]=[CH:22][C:21]([C:17]2[N:16]=[C:15]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[C:14]3[C:19](=[CH:20][C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=4)=[CH:12][CH:13]=3)[N:18]=2)=[CH:26][N:25]=1

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 675144285-[7-(3-Methanesulfonyl-phenyl)-4-morpholin-4-yl-quinazolin-2-yl]-pyridin-2-ylamine

Product 1

HCID 67514937{5-[7-(3-Methanesulfonyl-phenyl)-4-morpholin-4-yl-quinazolin-2-yl]-pyridine-2-yl}-carbamic acid 2,2,2-trichloroethyl esterYield 57,934.398%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (0° C.) of 5-[7-(3-methanesulfonyl-phenyl)-4-morpholin-4-yl-quinazolin-2-yl]-pyridin-2-ylamine (125 mg, 0.000271 mmol) in DCM (4 mL) was added 2,2,2-trichloroethylchloroformate (0.054 mL, 0.0004 mol) and TEA (0.056 mL, 0.0004 mol). The reaction mixture was allowed to stir at ambient temperature for 5 h. The volatiles were evaporated to get the crude product (100 mg). This material was taken to the next step without further purification.

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-5fc9d2e8e0a94ff4931121a2cab45b40
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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