Morpholine → 3-cyclopentyl-3-(4-(5-methoxy-2-(4-(morpholine-4-carbonyl)phenylamino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1876886Notes

Reaction equation

HRID 1876886 reaction equation
[C:1]([CH2:3][CH:4]([N:10]1[CH:14]=[C:13]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][N:18]=[C:17]([NH:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=3)[N:16]=2)[CH:12]=[N:11]1)[CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)#[N:2].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH:5]1([CH:4]([N:10]2[CH:14]=[C:13]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][N:18]=[C:17]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[O:30])=[CH:26][CH:25]=4)[N:16]=3)[CH:12]=[N:11]2)[CH2:3][C:1]#[N:2])[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 580145474-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)-5-methoxypyrimidin-2-ylamino)benzoic Acid

Product 1

HCID 580145703-cyclopentyl-3-(4-(5-methoxy-2-(4-(morpholine-4-carbonyl)phenylamino)pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)-5-methoxypyrimidin-2-ylamino)benzoic acid (25 mg, 0.058 mmol), morpholine (5.0 μL, 0.058 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (31 mg, 0.069 mmol) in N,N-dimethylformamide (0.4 mL) was added N,N-diisopropylethylamine (24 μL, 0.14 mmol). The reaction was stirred at room temperature for 1 h, quenched with water, purified on HPLC to give the desired product as a racemic mixture. LCMS (M+H) 502.5.

Workup

  1. customquenched with water
  2. custompurified on HPLC

Sources & evidence

ORD record
ord-3d7f7156a1ba40cb84d4b5c81f75258f
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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