HCID 15953240, compound → HCID 15953241, compound

HRID 271435Notes

Reaction equation

HRID 271435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([NH:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]3)[N:11]3[C:28](=[O:32])[N:29]([CH3:31])[N:30]=[C:10]3[C:9]=2[C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([NH:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][NH:18][CH2:17]3)[N:11]3[C:28](=[O:32])[N:29]([CH3:31])[N:30]=[C:10]3[C:9]=2[C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15953240HCID 15953240, compound

Product 1

HCID 15953241HCID 15953241, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (S)-tert-butyl 3-((7,8-bis(4-chlorophenyl)-2-methyl-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-ylamino)methyl)pyrrolidine-1-carboxylate (85 mg, 0.15 mmol) in a mixture of TFA (0.1 mL) and CH2Cl2 (0.5 mL) was stirred at room temperature until HPLC/MS indicated complete conversion to the title compound. The reaction mixture was then partitioned between EtOAc and saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried, and evaporated. The residue was purified by preparative reverse phase HPLC (without TFA) to obtain the title compound as a pale yellow solid. HPLC/MS: retention time 3.475 min, [M+H]30 =469.

Sources & evidence

ORD record
ord-89c1d8e2c6454836a559ceec41fe6e64
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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