Water → HCID 21182651, compound

HRID 1387115Notes

Reaction equation

HRID 1387115 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:16]([C:18]2[C:19]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:26][C:20]=3[S:21][C:22]=2[N:23]([CH3:25])[CH3:24])=[O:17])[CH:7]=[CH:8][C:9]=1[CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)([O-])=O.[BH4-].[Na+].O.[OH-].[Na+]>CCO.CO>[NH2:1][C:4]1[CH:5]=[C:6]([C:16]([C:18]2[C:19]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:26][C:20]=3[S:21][C:22]=2[N:23]([CH3:25])[CH3:24])=[O:17])[CH:7]=[CH:8][C:9]=1[CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 21182666HCID 21182666, compound

Product 1

HCID 21182651HCID 21182651, compound

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent2×

Conditions

Temperature
75 °C

Procedure

The 492 mg (0.955 mmol) of 6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-nitro-4-(1-pyrrolidinylmethyl)phenyl ketone (Part D, above) was dissolved in 21 mL of an EtOH/MeOH mixture (5:2 ratio). To the reaction mixture was added 1.07 g (4.77 mmol) of stannous chloride dihydrate. The reaction mixture was heated to 75° C. and to the solution was added 18.1 mg of sodium borohydride dissolved in 10 mL of EtOH/MeOH mixture (7:3 ratio). The solution was added dropwise via syringe over 25 min. The reaction mixture was stirred at 75° C. for 1.5 h. The reaction was then allowed to cool to room temperature. and was then poured into 20 mL of chilled (0° C.) water. The mixture was neutralized by adding 4 mL of 2 N NaOH solution and then concentrated under reduced pressure to a volume of 30 mL. This mixture was extracted with EtOAc (4×100 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to afford 451 mg (97% crude yield) as a orange foam.

Workup

  1. additionThe solution was added dropwise via syringe over 25 min
  2. temperatureto cool to room temperature
  3. additionand was then poured into 20 mL
  4. concentrationconcentrated under reduced pressure to a volume of 30 mL
  5. extractionThis mixture was extracted with EtOAc (4×100 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford 451 mg (97% crude yield) as a orange foam

Sources & evidence

ORD record
ord-da00c9828f74453fb54659023c5094c6
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…