Diisopropylethylamine → HCID 86713605, compound

HRID 2274232Notes

Reaction equation

HRID 2274232 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH3:20])=[CH:18][N:17]=[C:16]([NH:21][C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][C:23]=3[N+:31]([O-:33])=[O:32])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:34][N:35]1[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:20][C:19]1[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[N:15][C:16]([NH:21][C:22]2[CH:30]=[CH:29][C:25]([C:26](=[O:28])[NH:41][CH:38]3[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]3)=[CH:24][C:23]=2[N+:31]([O-:33])=[O:32])=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86713604HCID 86713604, compound

Product 1

HCID 86713605HCID 86713605, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-((4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methylpyrimidin-2-yl)amino)-3-nitrobenzoic acid (0.075 g, 0.164 mmol), 1-methylpiperidin-4-amine (37 mg, 0.33 mmol), HATU (140 mg, 0.37 mmol), and DIEA (0.1 mL, 0.6 mmol) in DMF (3.0 mL) was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc, washed with aqueous saturated sodium bicarbonate solution and saturated brine solution. The crude mixture was loaded onto silica gel and purified using 0-10% MeOH/DCM gradient containing 10% NH4OH to give the title compound (73 mg, 80%). MS (ES+) C27H38N8O5 requires: 554. Found: 555 [M+H]+

Workup

  1. washwashed with aqueous saturated sodium bicarbonate solution and saturated brine solution
  2. custompurified
  3. additioncontaining 10% NH4OH

Sources & evidence

ORD record
ord-d8bf38cc4edc4e25b44ea9e58bb6c11b
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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