Acetic Acid → HCID 69311128, compound

HRID 2219666Notes

Reaction equation

HRID 2219666 reaction equation
[N:1]1([NH:7][C:8](=[O:31])[CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]([C:21](=[O:29])[C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[C:11]=2[CH3:30])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:32]1(=O)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH:32]1([N:4]2[CH2:5][CH2:6][N:1]([NH:7][C:8](=[O:31])[CH2:9][C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=4)[N:12]([C:21](=[O:29])[C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[C:11]=3[CH3:30])[CH2:2][CH2:3]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 69310772HCID 69310772, compound

Product 1

HCID 69311128HCID 69311128, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.112 g (0.26 mmol) of N-(piperazin-1-yl)-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetamide and 0.03 mL (0.25 mmol) of cyclohexanone in 2 mL of anhydrous tetrahydrofuran was added 0.02 mL (0.32 mmol) of acetic acid then 0.078 g (0.37 mmol) of sodium triacetoxyborohydride. The reaction was stirred at room temperature for 20 hr then partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate (20 mL). The organic phase was washed with more bicarbonate (2×20 mL) then dried (MgSO4), filtered and evaporated. Preparative HPLC was used to isolate the title compound.

Workup

  1. customthen partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate (20 mL)
  2. washThe organic phase was washed with more bicarbonate (2×20 mL)
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6be6ad3b79464464bdf7957655e9d999
Source dataset
uspto-grants-2008_08
Patent number
US07414067B2

Reaction notes

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