Ethanol → HCID 18426271, compound

HRID 133624Notes

Reaction equation

HRID 133624 reaction equation
[CH:1](OCC)(OCC)OCC.[NH2:11][C:12]1[CH:39]=[CH:38][C:37]([Br:40])=[CH:36][C:13]=1[C:14]([NH:16][CH2:17][C:18]([NH:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)=[O:19])=[O:15].[BH4-].[Na+].C(O)C>ClCCl>[Br:40][C:37]1[CH:38]=[CH:39][C:12]([NH:11][CH3:1])=[C:13]([CH:36]=1)[C:14]([NH:16][CH2:17][C:18]([NH:20][CH2:21][CH:22]1[CH2:23][CH2:24][N:25]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[CH2:26][CH2:27]1)=[O:19])=[O:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 31214Ethyl orthoformateHCID 508820HCID 508820, compoundHCID 4311764Sodium borohydride

Product 1

HCID 18426271HCID 18426271, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A triethyl orthoformate (6.5 mL) solution of 4-[N-(2-amino-5-bromobenzoyl)glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1042) (50 mg, 0.10 mmol) was stirred at 150° C. for 17 hours and concentrated to thereby provide a yellow solid. Sodium borohydride (7.6 mg, 0.2 mmol) was added to an ethanol (3 mL) solution of the yellow solid, and the mixture was stirred at room temperature for 14 hours. The resulting white precipitate was dissolved in dichloromethane, and the obtained solution was washed with a 1 M aqueous solution of NaOH (2 mL). The organic layer was separated, dried over K2CO3, filtered and concentrated, and the obtained crude product was purified by column chromatography (SiO2, 20% methanol/chloroform) to provide 4-[N-[5-bromo-2-(methylamino)benzoyl]glycyl]aminomethyl-1-(4-chlorobenzyl)piperidine (Compd. No. 1427) (40 mg, 80%). The purity was determined by RPLC/MS (100%). ESI/MS m/e 505 (M++H, C23H28BrClF6N4O2).

Workup

  1. concentrationconcentrated
  2. customto thereby provide a yellow solid
  3. stirringthe mixture was stirred at room temperature for 14 hours
  4. washthe obtained solution was washed with a 1 M aqueous solution of NaOH (2 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over K2CO3
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe obtained crude product
  10. customwas purified by column chromatography (SiO2, 20% methanol/chloroform)

Sources & evidence

ORD record
ord-96864e651fc94109a48b09f52cd68c64
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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