Cyclopropanecarboxylic acid → HCID 86691851, compound

HRID 1616236Notes

Reaction equation

HRID 1616236 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:14]=3)=[CH:10][CH:11]=2)[N:6]([CH3:26])[C:5]1=[O:27].[CH:30]1([C:33]([OH:35])=O)[CH2:32][CH2:31]1.C(N(CC)[CH:40]([CH3:42])[CH3:41])(C)C.[CH3:45]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1.CO>[CH3:41][CH:40]([CH3:42])[CH2:45][C:10]1[CH:11]=[C:12]2[N:4]([CH2:3][C:2]([CH3:29])([CH3:28])[CH3:1])[C:5](=[O:27])[N:6]([CH3:26])[C:7]2=[N:8][C:9]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:33]([CH:30]3[CH2:32][CH2:31]3)=[O:35])[CH2:22][CH2:21]2)[CH:14]=1

Participants

7

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86691852HCID 86691852, compound

Product 1

HCID 86691851HCID 86691851, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(2,2-dimethylpropyl)-3-methyl-5-[3-(piperazin-1-ylmethyl)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (46-1) (50 mg, 0.13 mmol, 1.0 eq.) was dissolved in NMP (0.50 mL). Cyclopropanecarboxylic acid (16.4 mg, 0.19 mmol, 1.5 eq.) was added followed by N,N-diisopropylethylamine (0.07 mL, 0.38 mmol, 3.0 eq.) and HATU (72.5 mg, 0.19 mmol, 1.5 eq). The reaction stirred at ambient temperature for 5 minutes. The reaction was diluted with methanol, passed through a syringe filter and purified by reverse phase chromatography (15-95% H2O/Acetonitrile with 0.1% TFA modifier over 15 minutes) to afford 2-methylpropyl 5-(3-{[4-(cyclopropylcarbonyl)piperazin-1-yl]methyl}phenyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (48-1) as a white solid. HRMS (M+H)+: observed=462.2862, calculated=462.2864.

Workup

  1. custompassed through a syringe
  2. filtrationfilter
  3. custompurified by reverse phase chromatography (15-95% H2O/Acetonitrile with 0.1% TFA modifier over 15 minutes)

Sources & evidence

ORD record
ord-f5f3a7e7cfe6436b8616c389d89037e8
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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