((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide → ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide

HRID 1366388Notes

Reaction equation

HRID 1366388 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]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[N:27]=[C:26]([CH3:36])[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]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[N:27]=[C:26]([CH3:36])[N:25]=2)=[O:21])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 86636916((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide

Product 1

HCID 58000728((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamideYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

((2R)-2-(Cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide (90 mg, 0.18 mmol) was dissolved in 3 mL of MeOH, degassed and placed under argon. 10% Pd/C (18 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon for approximately 3 hrs. The contents were then degassed and filtered through Celite, and the Celite pad was washed with DCM and MeOH. The resulting filtrate was concentrated in vacuo to provide the pure ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-2-methyl-6-(1-pyrrolidinyl)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide (42 mg, 57%). LCMS: (M+H)+: 407.6.

Workup

  1. customdegassed
  2. addition10% Pd/C (18 mg) was added
  3. customthe contents were thoroughly degassed
  4. customfor approximately 3 hrs
  5. customThe contents were then degassed
  6. filtrationfiltered through Celite
  7. washthe Celite pad was washed with DCM and MeOH
  8. concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-02a0d0104e7945399f6e2aa326d814b6
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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