Diisopropylethylamine → 1-(7-Amino-3-(6-phenylpyridin-3-yl)-5-(1-(pyridin-3-ylmethyl)piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

HRID 2047183Notes

Reaction equation

HRID 2047183 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:3]=1[C:29](=[O:31])[CH3:30].Br[CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1.CCN(C(C)C)C(C)C>C1COCC1>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]([CH:23]2[CH2:24][CH2:25][N:26]([CH2:33][C:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)[CH2:27][CH2:28]2)[C:3]=1[C:29](=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2459343-(Bromomethyl)pyridineHCID 667379881-(7-Amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

Product 1

HCID 674941911-(7-Amino-3-(6-phenylpyridin-3-yl)-5-(1-(pyridin-3-ylmethyl)piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone (0.049 mmol, 20 mg), 3-(bromomethyl)pyridine (0.049 mmol, 12 mg) and DIEA (0.29 mmol, 37 mg) in THF (2 mL) was stirred at room temperature overnight. Concentration and purification by prep-LC afforded 1-(7-amino-3-(6-phenylpyridin-3-yl)-5-(1-(pyridin-3-ylmethyl)piperidin-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone: LCMS tR=2.71 Min (10 min run, UV254nm). Mass calculated for, M+ 503.24, observed LC/MS m/z 503.99 (M+H).

Workup

  1. concentrationConcentration and purification

Sources & evidence

ORD record
ord-4f549908f44b406d9485c2cfbcec7ee5
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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