Acetic Acid → HCID 66786496, compound

HRID 1096489Notes

Reaction equation

HRID 1096489 reaction equation
[ClH:1].[C:2]1([S:8]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]4[CH2:20][CH2:21][NH:22][CH2:23][C:13]([C:14]=34)=[CH:12]2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:25].[Na+].C(O)(=O)C.C(=O)C.Cl>C1COCC1>[ClH:1].[CH2:24]([N:22]1[CH2:21][CH2:20][C:15]2[C:14]3[C:13](=[CH:12][N:11]([S:8]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)(=[O:10])=[O:9])[C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH2:23]1)[CH3:25]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 66786661HCID 66786661, compound

Product 1

HCID 66786496HCID 66786496, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1-(Phenylsulfonyl)-3,4,5,6-tetrahydro-1H-azepino[3,4,5-cd]indole hydrochloride, Example 12 (70 mg, 0.2 mmol) was dissolved in THF (4 mL) before sodium triacetoxyborohydride (142 mg, 0.7 mmol) and acetic acid (134 mg, 2.2 mmol) was added. acetaldehyde (14.7 mg, 0.3 mmol) was added and the reaction mixture was heated in MW at 70° C. for 600 s. The reaction mixture was evaporated and the crude product was purified by preparative HPLC (33-63), using Xterra column. The product was isolated and transformed to the hydrochloride. 12.9 mg of the pure product was isolated as a clear oil. MS m/z 341 [M+H]+.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. customthe crude product was purified by preparative HPLC (33-63)
  4. customThe product was isolated

Sources & evidence

ORD record
ord-5624536f1c7348c6a18b240c66512294
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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