Dimethylformamide → HCID 58014468, compound

HRID 1876895Notes

Reaction equation

HRID 1876895 reaction equation
[C:1]([CH2:3][CH:4]([N:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[N:17]=2)[CH:13]=[N:12]1)[CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)#[N:2].[O:32]1[CH2:37][CH2:36][CH:35]([NH2:38])[CH2:34][CH2:33]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.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[C:1]([CH2:3][CH:4]([N:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([NH:38][CH:35]4[CH2:36][CH2:37][O:32][CH2:33][CH2:34]4)=[O:28])=[CH:30][CH:31]=3)[N:17]=2)[CH:13]=[N:12]1)[CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)#[N:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4192234-AminotetrahydropyranHCID 68754988HCID 68754988, compound

Product 1

HCID 58014468HCID 58014468, compound

Procedure

To a mixture of 4-[(4-{1-[2-cyano-1-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrazol-4-yl}pyrimidin-2-yl)amino]benzoic acid (20 mg, 0.00005 mol), tetrahydro-2H-pyran-4-amine (4.8 mg, 0.000048 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (25 mg, 0.000057 mol) in N,N-dimethylformamide (0.3 mL, 0.004 mol) was added N,N-diisopropylethylamine (20 μL, 0.00011 mol). The reaction was stirred at room temperature for 1 h, quenched with water, purified on HPLC to obtain the desired product as a racemic mixture (free base). LCMS (M+H) 502.4.

Workup

  1. customquenched with water
  2. custompurified on HPLC

Sources & evidence

ORD record
ord-ca854f524e7c46f2b1e21f69aac556b5
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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