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Water → Pentanoic acid [6-benzyl-4-(2-chloro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-amide

HRID 1020007
Notes
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Reaction equation

HRID 1020007 reaction equation
CO[C:3]([CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1)=O.[ClH:19].[NH2:20][C:21]([NH2:23])=[NH:22].[C:24](=[O:27])([O-])[O-].[K+].[K+].O>CN(C=O)C.CO>[CH2:12]([N:7]1[CH2:8][CH2:9][C:10]2[N:22]=[C:21]([NH:23][C:24](=[O:27])[CH2:3][CH2:5][CH2:10][CH3:9])[N:20]=[C:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:5]=2[CH2:6]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 107480Methyl 1-benzyl-4-oxo-3-piperidinecarboxylate

Product 1

HCID 46937260Pentanoic acid [6-benzyl-4-(2-chloro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-amideYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6228DimethylformamideSolvent

Procedure

Methyl-1-benzyl-4-oxo-3-piperidine carboxylate (5.68 g., 20 mmoles) and guanidine hydrochloride (2.0 g., 21 mmoles) were suspended and stirred in dry DMF (45 mls) before potassium carbonate (5.68 g., 41 mmoles) was added portionwise over 15 minutes. The reaction mixture was poured onto cold water (750 mls) to release a white/beige solid which was rapidly stirred for 30 minutes. The solid was filtered washed with water (100 mls) and dried in a vacuum desiccator. The product was then slurried in ether (150 mls), filtered and dried in vacuo overnight, to leave an off-white solid (4.46 g., 87% yield). Single spot by tlc (MeOH, Rf 0.66), LC-MS (retention 2.20 mins., mass 257 M+H).

Workup

  1. additionwas added portionwise over 15 minutes
  2. filtrationThe solid was filtered
  3. washwashed with water (100 mls)
  4. customdried in a vacuum desiccator
  5. filtrationfiltered
  6. customdried in vacuo overnight
  7. customto leave an off-white solid (4.46 g., 87% yield)

Sources & evidence

ORD record
ord-52fae9d42e2e45bc97532e3e142d46a0
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716302B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes