Diisopropylethylamine → HCID 44250960, compound

HRID 1409197Notes

Reaction equation

HRID 1409197 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.[C:26]1([S:32]([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CS(C)=O.CO>[OH:23][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:4]2[CH:3]=[C:2]([N:38]3[CH2:37][CH2:36][CH:35]([S:32]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)(=[O:33])=[O:34])[CH2:40][CH2:39]3)[N:7]3[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]3[N:5]=2)=[O:24])=[CH:15][CH:16]=1)([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 177498034-(Benzenesulfonyl)piperidine--hydrogen chloride (1/1)HCID 86652267N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide

Product 1

HCID 44250960HCID 44250960, compoundYield 73%

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), 4-(phenylsulfonyl)piperidine hydrochloride (145 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 (40-55% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (97.2 mg, 73%). 1H NMR (DMSO-d6) δ: 10.90 (s, 1H), 7.99 (d, J=8.8 Hz, 2H), 7.89-7.95 (m, 2H), 7.78-7.85 (m, 1H), 7.68-7.76 (m, 2H), 7.60 (d, 2H), 7.28 (s, 1H), 6.18 (s, 1H), 4.53 (d, J=12.6 Hz, 2H), 3.69 (tt, J=11.8, 3.7 Hz, 1H), 3.00-3.11 (m, 2H), 2.37 (s, 3H), 2.04 (d, J=10.9 Hz, 2H), 1.75 (qd, J=12.3, 3.8 Hz, 2H), 1.45 (s, 6H); ESI-MS: m/z 534.2 (M+H)+.

Workup

  1. customwas then purified by preparatory HPLC (40-55% MeCN/H2O gradient+0.01% TFA)

Sources & evidence

ORD record
ord-a0af856877324615bb215e50dc2a49ba
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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