Hydrochloric Acid → HCID 51035721, compound

HRID 1054428Notes

Reaction equation

HRID 1054428 reaction equation
[Na].[CH2:2]([N:9]1[CH2:15][CH2:14][CH2:13][NH:12]/[C:11](=[C:16]2/[C:17]([CH2:29][C:30]([O:32]C)=O)=[N:18][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:20]/2=[O:21])/[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CO.O>[CH2:2]([N:9]1[CH2:15][CH2:14][CH2:13][N:12]2[C:30](=[O:32])[CH:29]=[C:17]3[NH:18][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:28])[C:20](=[O:21])[C:16]3=[C:11]2[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 178499636HCID 178499636, compound

Product 1

HCID 51035721HCID 51035721, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

An isopropanolic solution of MeONa, obtained by dissolving of sodium (0.055 g, 2.4 mmol, 2 eq.) in MeOH (3 ml) under nitrogen, was treated with methyl [(4Z)-4-(4-benzyl-1,4-diazepan-2-ylidene)-1-(2-chlorophenyl)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (II) (530 mg, 1.2 mmol, 1 eq.). The reaction mixture was stirred at room temperature for 0.5 h, then cooled, diluted with water (8 mL) and neutralized to pH 6 by addition 1M HCl solution. The precipitate was filtered off and dried under vacuo. The crude was purified by flash chromatography to yield 129 mg of pure product 10-benzyl-2-(2-chlorophenyl)-2,3,8,9,10,11-hexahydro-1H-pyrazolo[4′,3′:3,4]pyrido [1,2-a][1,4]diazepine-1,5(7H)-dione. Yield 26%. 1HNMR (500 MHz, DMSO-d6): 1.62-1.68 (m, 2H); 2.83 (t, 2H, J=7.5 Hz); 3.62-3.66 (m, 2H); 4.40-4.76 (m, 2H); 5.73 (s, 1H); 7.21-7.32 (m, 5H); 7.44-7.50 (m, 2H); 7.55-7.60 (m, 1H); 7.61-7.67 (m, 1H); 10.75-10.68 (bs, 1H). MS (ESI+): 421.9.

Workup

  1. temperaturecooled
  2. filtrationThe precipitate was filtered off
  3. customdried under vacuo
  4. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-e16dcefae43d42629da9ec511b56a009
Source dataset
uspto-grants-2016_07
Patent number
US09394306B2

Reaction notes

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