Acetic Acid → HCID 178493021, compound

HRID 992087Notes

Reaction equation

HRID 992087 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](N=[CH:8][CH:9]=[N:10]2)=[C:5]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:4]=1.[C:19]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH3:30])[CH:25]=[C:24]2[CH:31]1[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]1)#[N:20].[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:38]=[CH:8][CH:9]=[N:10]2)=[C:5]([N:13]2[CH2:14][CH2:15][N:16]([C@@H:34]3[CH2:35][CH2:36][C@H:31]([C:24]4[C:23]5[C:27](=[CH:28][CH:29]=[C:21]([C:19]#[N:20])[CH:22]=5)[N:26]([CH3:30])[CH:25]=4)[CH2:32][CH2:33]3)[CH2:17][CH2:18]2)[CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 154812824-(5-Cyano-1-methyl-3-indolyl)cyclohexanoneHCID 18414135HCID 18414135, compound

Product 1

HCID 178493021HCID 178493021, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 7-methoxy-5-piperazin-1-yl-quinoxaline (160 mg, 0.66 mmol), 4-(5-cyano-1-methyl-1H-indol-3-yl)-cyclohexanone (170 mg, 0.66 mmol), and sodium triacetoxyborohydride (210 mg, 0.98 mmol) in dichloroethane (30 mL) was added acetic acid (0.1 mL, 1.3 mmol) and stirred overnight at room temperature. The reaction was quenched with 1 M NaOH (100 mL) then extracted in CH2Cl2 (75 mL) and EtOAc (100 mL). The organic fractions were combined, dried over Na2SO4, concentrated, filtered and chromatographed (5% MeOH/EtOAc) affording 120 mg (38%) of the cis isomer as a bright yellow solid: mp 226-229° C.

Workup

  1. customThe reaction was quenched with 1 M NaOH (100 mL)
  2. extractionthen extracted in CH2Cl2 (75 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customchromatographed (5% MeOH/EtOAc)
  7. customaffording 120 mg (38%) of the cis isomer as a bright yellow solid

Sources & evidence

ORD record
ord-b6c9a3d2b2104a429665c791aac8e240
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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