Dimethylformamide → 3-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)-N-(tetrahydro-2H-pyran-4-yl)benzamide

HRID 1876900Notes

Reaction equation

HRID 1876900 reaction equation
[C:1]([CH2:3][CH:4]([N:8]1[CH:12]=[C:11]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([NH:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=O)[N:14]=2)[CH:10]=[N:9]1)[CH:5]1[CH2:7][CH2:6]1)#[N:2].[O:31]1[CH2:36][CH2:35][CH:34]([NH2:37])[CH2:33][CH2:32]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:8]1[CH:12]=[C:11]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([NH:21][C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([NH:37][CH:34]3[CH2:35][CH2:36][O:31][CH2:32][CH2:33]3)=[O:27])[N:14]=2)[CH:10]=[N:9]1)[CH:5]1[CH2:7][CH2:6]1)#[N:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 4192234-AminotetrahydropyranHCID 687585973-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)benzoic Acid

Product 1

HCID 580143853-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)-N-(tetrahydro-2H-pyran-4-yl)benzamide

Procedure

To a mixture of 3-({4-[1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl]-5-methoxypyrimidin-2-yl}amino)benzoic acid (30 mg, 0.00007 mol), tetrahydro-2H-pyran-4-amine (7.5 mg, 0.000074 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (39 mg, 0.000089 mol) in N,N-dimethylformamide (0.5 mL, 0.006 mol) was added N,N-diisopropylethylamine (31 μL, 0.00018 mol). The reaction was stirred at room temperature for 1 h, quenched with water, purified on HPLC to give the desired product as a diastereomeric mixture (free base). LCMS (M+H) 488.2.

Workup

  1. customquenched with water
  2. custompurified on HPLC

Sources & evidence

ORD record
ord-22b45a19b5a5414192404e505a0cd067
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

Loading…