Acetic Acid → HCID 66785162, compound

HRID 1096504Notes

Reaction equation

HRID 1096504 reaction equation
[O:1]=[C:2]1[C:8]2=[CH:9][N:10]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:11]3[CH:12]=[CH:13][CH:14]=[C:6]([C:7]=32)[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[C:31]([OH:37])([C:33]([F:36])([F:35])[F:34])=[O:32].[BH4-].[Na+].C(O)(=O)C>C(Cl)Cl>[F:34][C:33]([F:36])([F:35])[C:31]([OH:37])=[O:32].[C:18]1([S:15]([N:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:6]4[CH2:5][NH:4][CH2:3][CH:2]([OH:1])[C:8]([C:7]=34)=[CH:9]2)(=[O:17])=[O:16])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 59848832HCID 59848832, compound

Product 1

HCID 66785162HCID 66785162, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-oxo-1-(phenylsulfonyl)-1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate Intermediate 18 (11 mg, 0.03 mmol) was dissolved in DCM (1 ml). TFA (0.5 ml) was added and the solution was heated to boiling, and then evaporated. The residue was dissolved in EtOH (3 ml). Sodium borohydride (7.5 mg, 0.2 mmol) was added. The reaction mixture was stirred at room temperature for 45 min. The solution was acidified with acetic acid, and evaporated. The evaporation procedure was repeated twice with the addition of methanol. The crude product was purified by preparative HPLC (ACE C8 5 mm, water containing 0.1% TFA-CH3CN) to give the title compound, 7 mg.

Workup

  1. temperaturethe solution was heated
  2. customevaporated
  3. dissolutionThe residue was dissolved in EtOH (3 ml)
  4. customevaporated
  5. customThe evaporation procedure
  6. additionwas repeated twice with the addition of methanol
  7. customThe crude product was purified by preparative HPLC (ACE C8 5 mm, water containing 0.1% TFA-CH3CN)

Sources & evidence

ORD record
ord-402c77a519bc4c99ac3cbf9b76b0aa17
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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