Acetic Acid → HCID 11628613, compound

HRID 2378090Notes

Reaction equation

HRID 2378090 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:23]=2[N:22]([CH3:24])[C:21]([C:25](=[O:44])[NH:26][C:27]2[CH:32]=[C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:30]=[C:29]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:28]=2[O:42][CH3:43])=[CH:20]3)[CH2:10][CH2:9]1)=[O:7])(C)(C)[CH3:2].CCOC(N1CCNCC1)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:23]=2[N:22]([CH3:24])[C:21]([C:25](=[O:44])[NH:26][C:27]2[CH:32]=[C:31]([C:33]([CH3:35])([CH3:36])[CH3:34])[CH:30]=[C:29]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[C:28]=2[O:42][CH3:43])=[CH:20]3)[CH2:12][CH2:13]1)=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 11563567HCID 11563567, compound

Product 1

HCID 11628613HCID 11628613, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 7-formyl-1-methyl-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (see Example 2, 30 mg, 0.066 mmol) and ethyl N-piperazinocarboxylate (104 mg, 0.66 mmol) in dichloroethane (2 mL) was added acetic acid (0.1 mL). The mixture was stirred at room temperature for 4 h. Sodium triacetoxyborohydride (35 mg, 0.156 mmol) was then added to the reaction mixture. The reaction was stirred overnight at room temperature and then quenched with saturated NaHCO3 solution. The mixture was then extracted with EtOAc and dichloromethane in sequence, dried over Na2SO4 and concentrated. The residue was purified by preparative-TLC, eluting with EtOAc-hexane, 1:1, providing 15 mg (38%) of the title compound. ESI MS m/z 600.37 [M+H]+.

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. customquenched with saturated NaHCO3 solution
  3. extractionThe mixture was then extracted with EtOAc and dichloromethane in sequence
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative-TLC,
  7. washeluting with EtOAc-hexane, 1:1

Sources & evidence

ORD record
ord-3ae6967227ca4e06b14dee01792f7869
Source dataset
uspto-grants-2008_12
Patent number
US07470692B2

Reaction notes

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