Hydrochloric Acid → HCID 20061003, compound

HRID 1085140Notes

Reaction equation

HRID 1085140 reaction equation
[CH3:1][C:2]1[C:3]([CH3:32])=[CH:4][C:5]2[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[CH2:9][C:8]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:29]5[CH:28]=[CH:27][N:26]=[CH:25][C:24]=5[N:23]=[C:22]4[CH3:30])=[CH:17][CH:16]=3)=[N:7][C:6]=2[CH:31]=1.Cl.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1[C:3]([CH3:32])=[CH:4][C:5]2[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[CH2:9][CH:8]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[C:29]5[CH:28]=[CH:27][N:26]=[CH:25][C:24]=5[N:23]=[C:22]4[CH3:30])=[CH:17][CH:16]=3)[NH:7][C:6]=2[CH:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 10341961HCID 10341961, compound

Product 1

HCID 20061003HCID 20061003, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8,9-dimethyl-5-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenyl]-4H-imidazo[1,2-a][1,5]-benzodiazepine (100 mg, 0.24 mmol) in dichloromethane was stirred with an excess of ethereal hydrogen chloride until precipitation was complete. The solid was filtered and dissolved in dry methanol (5 ml) to which was added sodium cyanoborohydride (20 mg 0.32 mmol). After stirring for 16 hours, the solution was acidified with dilute hydrochloric acid then adjusted to pH 8 by addition of sodium bicarbonate solution. The mixture was extracted with ethyl acetate which was dried over magnesium sulphate. Evaporation left a colourless gum.

Workup

  1. customuntil precipitation
  2. filtrationThe solid was filtered
  3. dissolutiondissolved in dry methanol (5 ml) to which
  4. extractionThe mixture was extracted with ethyl acetate which
  5. dry with materialwas dried over magnesium sulphate
  6. customEvaporation
  7. waitleft a colourless gum

Sources & evidence

ORD record
ord-8556595c687d41ce9df25406c01b815d
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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