Acetic Acid → HCID 178486623, compound

HRID 992088Notes

Reaction equation

HRID 992088 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[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(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.Cl>ClC(Cl)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N:13]3[CH2:14][CH2:15][N:16]([C@@H:34]4[CH2:33][CH2:32][C@H:31]([C:24]5[C:23]6[C:27](=[CH:28][CH:29]=[C:21]([C:19]#[N:20])[CH:22]=6)[N:26]([CH3:30])[CH:25]=5)[CH2:36][CH2:35]4)[CH2:17][CH2:18]3)[N:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 154812824-(5-Cyano-1-methyl-3-indolyl)cyclohexanoneHCID 184140846-Methoxy-8-piperazin-1-yl-[1,7]naphthyridine

Product 1

HCID 178486623HCID 178486623, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-methoxy-8-piperazin-1-yl-[1,7]naphthyridine (250 mg, 1.02 mmol), 4-(5-cyano-1-methyl-1H-indol-3-yl)-cyclohexanone (260 mg, 1.02 mmol), and sodium triacetoxyborohydride (320 mg, 1.53 mmol) in dichloroethane (50 mL) was added acetic acid (0.12 mL, 2.04 mmol) and stirred overnight at room temperature. The reaction was quenched with 1 M NaOH (50 mL) then extracted in CH2Cl2 (1×50 mL) and EtOAc (75 mL). The organic fractions were combined, dried over Na2SO4, concentrated, filtered and chromatographed (5% MeOH/EtOAc+NH4OH) affording 160 mg (33%) of the cis isomer as a yellow foam. The HCl salt was generated form EtOAc affording a pale yellow solid: mp 235-238° C.

Workup

  1. customThe reaction was quenched with 1 M NaOH (50 mL)
  2. extractionthen extracted in CH2Cl2 (1×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customchromatographed (5% MeOH/EtOAc+NH4OH)
  7. customaffording 160 mg (33%) of the cis isomer as a yellow foam

Sources & evidence

ORD record
ord-80485981a0f8450f88d3c7279dda260a
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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