Sodium Bicarbonate → HCID 24771917, compound

HRID 1696176Notes

Reaction equation

HRID 1696176 reaction equation
[C:1]([C:4]1([NH:10][C:11]([C:13]2[CH:14]=[N:15][N:16]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)=[C:20]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[Cl:35])[CH:19]=[N:18][C:17]=23)=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(O)=[O:2].Cl.CN.O.O[N:41]1[C:45]2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[Cl:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:20]1[CH:19]=[N:18][C:17]2[N:16]([N:15]=[CH:14][C:13]=2[C:11](=[O:12])[NH:10][C:4]2([C:1](=[O:2])[NH:41][CH3:45])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[C:21]=1[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1

Participants

8

Reactant 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 24772846HCID 24772846, compound

Product 1

HCID 24771917HCID 24771917, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of the compound obtained in Example A4 (50 mg) and methylamine hydrochloride (8 mg) in methylene chloride (1 mL) were added 1-hydroxybenzotriazole monohydrate (23 mg), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (29 mg) and triethylamine (21 μL), and the mixture was stirred at room temperature overnight. To the reaction mixture were added methylene chloride and an aqueous saturated sodium hydrogencarbonate solution. After stirring vigorously for 10 minutes, the organic layer was separated and concentrated in vacuo. The resultant crude product was purified by column chromatography on silica gel (solvent; chloroform/methanol=100/0 to 95/5) and triturated to give 6-(2-chlorophenyl)-7-(4-chlorophenyl)-3-[N-[1-(N-methylcarbamoyl)cyclohexyl]-carbamoyl]pyrazolo[1,5-a]pyrimidine (25 mg; yield: 61%)

Workup

  1. stirringAfter stirring vigorously for 10 minutes
  2. customthe organic layer was separated
  3. concentrationconcentrated in vacuo
  4. customThe resultant crude product was purified by column chromatography on silica gel (solvent; chloroform/methanol=100/0 to 95/5)
  5. customtriturated

Sources & evidence

ORD record
ord-aee0245c6fe74a65a3aa51778de2707c
Source dataset
uspto-grants-2012_04
Patent number
US08163759B2

Reaction notes

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