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

HRID 1366390Notes

Reaction equation

HRID 1366390 reaction equation
[N:1]1([C:5]2[N:10]=[C:9]([CH2:11][CH3:12])[N:8]=[C:7]([NH:13][NH:14][C:15](=[O:35])[C@H:16]([CH2:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:17][N:18]([O:21]CC3C=CC=CC=3)[CH:19]=[O:20])[C:6]=2[F:36])[CH2:4][CH2:3][CH2:2]1>CO>[N:1]1([C:5]2[N:10]=[C:9]([CH2:11][CH3:12])[N:8]=[C:7]([NH:13][NH:14][C:15](=[O:35])[C@H:16]([CH2:29][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[CH2:17][N:18]([OH:21])[CH:19]=[O:20])[C:6]=2[F:36])[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 86636917[(2R)-3-{2-[6-(1-azetidinyl)-2-ethyl-5-fluoro-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

Product 1

HCID 58000517[(2R)-3-{2-[6-(1-azetidinyl)-2-ethyl-5-fluoro-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamideYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(2R)-3-{2-[6-(1-Azetidinyl)-2-ethyl-5-fluoro-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (160 mg, 0.32 mmol) was dissolved in 10 mL of MeOH, degassed and placed under argon. 5% Pd/C (40 mg) was added, and the contents were thoroughly degassed and stirred under a hydrogen balloon until the reaction was deemed complete by LCMS. 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 [(2R)-3-{2-[6-(1-azetidinyl)-2-ethyl-5-fluoro-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (100 mg, 76%). LCMS: (M+H)+: 409.2.

Workup

  1. customdegassed
  2. addition5% Pd/C (40 mg) was added
  3. customthe contents were thoroughly degassed
  4. customThe contents were then degassed
  5. filtrationfiltered through Celite
  6. washthe Celite pad was washed with DCM and MeOH
  7. concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-edacc1cdc60147ba9716796368b9585a
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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