Hydrochloric Acid → (R)-7-cyano-2,3,4,5-tetrahydro-1-[(((1,1-dimethylethoxy)-carbonyl)-1H-imidazol-4-yl)methyl]-4-(methylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepine

HRID 1282703Notes

Reaction equation

HRID 1282703 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][N:8]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=3[CH2:12][N:11]([S:21]([CH3:24])(=[O:23])=[O:22])[C@H:10]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:9]2)[N:4]=[CH:3]1.C1C([N+]([O-])=O)=CC=C([Cl-][C:42]([O-:44])=[O:43])C=1.Cl>C1COCC1>[C:19]([C:17]1[CH:16]=[CH:15][C:14]2[N:8]([CH2:7][C:5]3[N:4]=[CH:3][N:2]([C:42]([O:44][C:13]([CH3:18])([CH3:14])[CH3:12])=[O:43])[CH:6]=3)[CH2:9][C@@H:10]([CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:11]([S:21]([CH3:24])(=[O:22])=[O:23])[CH2:12][C:13]=2[CH:18]=1)#[N:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178504922HCID 178504922, compound

Product 1

HCID 69841490(R)-7-cyano-2,3,4,5-tetrahydro-1-[(((1,1-dimethylethoxy)-carbonyl)-1H-imidazol-4-yl)methyl]-4-(methylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepineYield 116%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound C of Example 248 (200 mg, 0.76 mmol) in THF (20 mL) under argon was added 4-nitrophenylchloroformate (0.88 mL, 0.76 mmol). The solution was stirred for 8 hours, poured into aqueous hydrochloric acid (150 mL, 1N), extracted with ethyl acetate (2×150 mL), dried (MgSO4), and concentrated to an oil which was purified using flash chromatography (50 g silica, 2:1 hexane:ethyl acetate) to provide Compound A (230 mg, 70%) as a clear oil.

Workup

  1. extractionextracted with ethyl acetate (2×150 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to an oil which
  4. customwas purified

Sources & evidence

ORD record
ord-06a82328076c4514b31dfb04f012b1d6
Source dataset
uspto-grants-2002_09
Patent number
US06455523B1

Reaction notes

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