Diisopropylethylamine → HCID 67064660, compound

HRID 1409225Notes

Reaction equation

HRID 1409225 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH:3]=1.Cl.[N:26]1[N:27]=[CH:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][C:30]=12.C(N(CC)C(C)C)(C)C>CN(C=O)C.CS(C)=O.CO>[N:26]1[N:27]=[CH:28][N:29]2[CH2:34][CH2:33][N:32]([C:2]3[N:7]4[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]4[N:5]=[C:4]([NH:12][C:13](=[O:24])[C:14]4[CH:19]=[CH:18][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=4)[CH:3]=3)[CH2:31][C:30]=12

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 17998717HCID 17998717, compoundHCID 86652267N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide

Product 1

HCID 67064660HCID 67064660, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2F, 86 mg, 0.25 mmol), 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride (80 mg, 0.50 mmol), and N,N-diisopropylethylamine (116 mg, 0.90 mmol) in DMF (1.0 mL) was stirred at 100° C. for 2 h. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC (20-45% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (71.4 mg, 66%). ESI-MS: m/z 433.3 (M+H)+.

Workup

  1. customwas then purified by preparatory HPLC (20-45% MeCN/H2O gradient+0.01% TFA)

Sources & evidence

ORD record
ord-f47a8a0a7c0d47f98883ab51a7765522
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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