Ethyl orthoformate → HCID 18426271, compound

HRID 279346Notes

Reaction equation

HRID 279346 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:9])=[O:5].[BH4-].[Na+].[CH:33](OCC)(OCC)OCC>C(O)C.ClCCl>[Br:30][C:27]1[CH:28]=[CH:29][C:2]([NH:1][CH3:33])=[C:3]([CH:26]=1)[C:4]([NH:6][CH2:7][C:8]([NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)[CH2:16][CH2:17]1)=[O:9])=[O:5]

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 508820HCID 508820, compoundHCID 4311764Sodium borohydride

Product 1

HCID 18426271HCID 18426271, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-{N-(2-amino-5-bromobenzoyl)glycyl}aminomethyl-1-(4-chlorobenzyl)piperidine (Compound No. 1042) (50 mg, 0.10 mmol) in triethyl orthoformate (6.5 mL) was stirred at 150° C. for 17 h. Concentration afforded a yellow solid. To a solution of the yellow solid in ethanol (3 mL) was added sodium borohydride (7.6 mg, 0.2 mmol) and the mixture was stirred at room temperature for 14 h. A resulting white precipitate was resolved in dichloromethane and the solution was washed with 1 N aqueous NaOH (2 mL). The organic layer was separated, dried over K2CO3, filtered and evaporated. Column chromatography (SiO2, 20% MeOH/CHCl3) gave 4-[N-{5-bromo-2-(methylamino)benzoyl)glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compound No. 1427) (40 mg, 80%) The purity was determined by RPLC/MS (100%); ESI/MS m/e 505 (C23H28BrClF6N4O2).

Workup

  1. concentrationConcentration
  2. customafforded a yellow solid
  3. washthe solution was washed with 1 N aqueous NaOH (2 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over K2CO3
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-db8e942560d044f197891e0618b55ebc
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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