Ammonium Chloride → HCID 57642245, compound

HRID 2113326Notes

Reaction equation

HRID 2113326 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:43])[C:6]1[CH:11]=[C:10]([NH:12][CH3:13])[CH:9]=[C:8]([NH:14][C:15](=[O:42])[CH2:16][N:17]2[N:23]=[C:22]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[N:19]([CH2:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[C:18]2=[O:41])[CH:7]=1.[NH4+].[Cl-]>CO>[CH3:3][O:4][C:5](=[O:43])[C:6]1[CH:11]=[C:10]([NH:12][CH3:13])[CH:9]=[C:8]([NH:14][C:15](=[O:42])[CH2:16][N:17]2[N:23]=[C:22]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[N:19]([CH2:34][CH:35]([OH:40])[C:36]([CH3:38])([CH3:39])[CH3:37])[C:18]2=[O:41])[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 57642277HCID 57642277, compound

Product 1

HCID 57642245HCID 57642245, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
2.5 °C

Procedure

Sodium borohydride (5 mg, 0.13 mmol) was added to an ice-cooled solution of 3-{2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetylamino}-5-methylamino-benzoic acid methyl ester (Example 74)(64 mg, 0.11 mmol) in MeOH (2 ml). The reaction mixture was stirred at 0-5° C. for 40 mins, then at room temperature for 2 h. Saturated NH4Cl solution (10 ml) was added and the product was extracted with CHCl3 (15 ml). The organic phase was dried (MgSO4), filtered and the filtrate was evaporated to afford the title compound (60 mg, 97%). 1H NMR (CDCl3) 8.10-8.79 (1H, m), 7.55 (2H, m), 7.36 (2H, m), 7.24 (1H, m), 6.95 (1H, s), 6.70 (1H, m), 4.46 (1H, m), 4.29-4.04 (2H, m), 3.89 (4H, m), 3.82-3.60 (1H, m), 3.43-3.23 (1H, m), 2.81 (4H, m), 2.15-1.66 (7H, m), 1.33-1.24 (3H, m), 0.97 and 0.93 (9H, s×2). Found C, 63.17; H, 7.59; N, 11.85%; C31H41N5O5.1.5H2O requires C, 63.03, H, 7.51, N 11.86%.

Workup

  1. waitat room temperature for 2 h
  2. extractionthe product was extracted with CHCl3 (15 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b308f45698494e6bb8e4085da7d3a926
Source dataset
uspto-grants-2009_04
Patent number
US07524837B2

Reaction notes

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