Diisopropylethylamine → HCID 57920212, compound

HRID 216041Notes

Reaction equation

HRID 216041 reaction equation
Cl.[CH3:2][C:3]1([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[O:22][CH:21]=[N:20][CH:19]=3)[CH:13]=2)=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[C:24]1[C:25]2[C:32]([CH3:33])=[CH:31][NH:30][C:26]=2[N:27]=[CH:28][N:29]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH3:2][C:3]1([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[O:22][CH:21]=[N:20][CH:19]=3)[CH:13]=2)=[O:10])[CH2:4][CH2:5][N:6]([C:24]2[C:25]3[C:32]([CH3:33])=[CH:31][NH:30][C:26]=3[N:27]=[CH:28][N:29]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 68993419HCID 68993419, compound

Product 1

HCID 57920212HCID 57920212, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
105 °C

Procedure

A pressure vessel was charged with a solution of 4-methyl-N-(3-(oxazol-5-yl)phenyl)piperidine-4-carboxamide hydrochloride from step B (51.9 mg, 0.17 mmol) and isopropanol (3 mL), and to this solution was added 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (55.0 mg, 0.329 mmol) and N,N-diisopropylethylamine (297.9 mg, 0.40 mL, 2.31 mmol). The vessel was sealed, and the reaction was heated to 105° C. for 15 hours. The reaction was worked up by normal means, and the residue was purified by prep HPLC to afford the title compound as an off-white solid.

Workup

  1. customThe vessel was sealed
  2. customthe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-4d775e918c2b4c3a9860be381b4a6b5e
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

Loading…