Sodium triacetoxyborohydride → HCID 58525004, compound

HRID 1944599Notes

Reaction equation

HRID 1944599 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12]O)=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[C:17]([C:34]([F:37])([F:36])[F:35])[CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:52][NH2:53].Cl>ClCCl.C1COCC1.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][NH:53][CH3:52])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:23][CH2:22]2)=[C:17]([C:34]([F:37])([F:35])[F:36])[CH:16]=1

Participants

7

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 6364545Methylamine hydrochlorideHCID 58525018HCID 58525018, compound

Product 1

HCID 58525004HCID 58525004, compound

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(4-(6-chloro-3-(hydroxymethyl)quinolin-4-ylamino)-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (400 mg, 0.74 mmol) in dichloromethane (10 mL) at room temperature was added MnO2 (2 g). The resultant solution was stirred for 3 h before filtering through celite and washing with dichloromethane (20 mL). After removal solvent in vacuo, the residue was redisolved in THF (5 mL), to which NaBH(OAc)3 (443 mg, 2.1 mmol) and CH3NH2HCl (140 mg, 2.1 mmol) were added. The solution was stirred at room temperature overnight, quenched with NaHCO3 (sat. 10 mL), extracted with EtOAc (20 mL×3), and dried over Na2SO4. After removal of solvent in vacuo, the crude product was taken to next step without further purification. LC-MS: (M+H)=550.32

Workup

  1. filtrationbefore filtering through celite
  2. washwashing with dichloromethane (20 mL)
  3. customAfter removal solvent in vacuo
  4. additionwere added
  5. customquenched with NaHCO3 (sat. 10 mL)
  6. extractionextracted with EtOAc (20 mL×3)
  7. dry with materialdried over Na2SO4
  8. customAfter removal of solvent in vacuo
  9. customthe crude product was taken to next step without further purification

Sources & evidence

ORD record
ord-83ca01cd8da748ac92bebbcfe1c80205
Source dataset
uspto-grants-2013_03
Patent number
US08394818B2

Reaction notes

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