[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide → [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide

HRID 1366465Notes

Reaction equation

HRID 1366465 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[N:27]=[C:26]([CH3:39])[N:25]=2)=[O:21])[CH2:8][N:9]([O:12]CC2C=CC=CC=2)[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[N:27]=[C:26]([CH3:39])[N:25]=2)=[O:21])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86636947[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide

Product 1

HCID 58000670[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamideYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.0999 g, 0.1867 mmol) was dissolved in 10 mL of MeOH, degassed and placed under nitrogen. Then 10% Pd(C) (0.025 g) was added and the contents were degassed and stirred under a hydrogen balloon for 2.75 h. The contents were then degassed and filtered through an Acrodisc (CR PTFE 0.45 μm). The resulting filtrate was concentrated and purified by RP-HPLC to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[(2-pyridinylmethyl)amino]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide as a beige solid (0.0231 g, 28%). LCMS: (M+H)+=446.5.

Workup

  1. customdegassed
  2. additionThen 10% Pd(C) (0.025 g) was added
  3. customthe contents were degassed
  4. customThe contents were then degassed
  5. filtrationfiltered through an Acrodisc (CR PTFE 0.45 μm)
  6. concentrationThe resulting filtrate was concentrated
  7. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-460d0c27474f4870a0a0a5d47e7d537c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…