Acetic Acid → HCID 66787210, compound

HRID 1096488Notes

Reaction equation

HRID 1096488 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)C.[Na+].C(O)(=O)C.C=O.Cl>C1COCC1>[ClH:1].[CH3:24][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

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66786661HCID 66786661, compound

Product 1

HCID 66787210HCID 66787210, compoundYield 12%

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 (100 mg, 0.3 mmol) was dissolved in THF (4 mL) before sodium triacetoxyborohydride (203 mg, 1.0 mmol) and acetic acid (191 mg, 3.2 mmol) was added. Aqueous formaline (37%, 1 mL) was added and the reaction mixture was heated in MW at 70° C. for 300 s. The reaction mixture was evaporated and the crude product was purified by preparative HPLC using System B, 100 mM NH4HCO3/MeCN (36-66% MeCN). The product was isolated and transformed to the hydrochloride. 15.2 mg of the pure product was isolated as an yellow oil, yield 12%. MS m/z 327 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-237daa39073b486c8389f4165e3007ae
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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