HCID 86636927, compound → [(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide

HRID 1366407Notes

Reaction equation

HRID 1366407 reaction equation
[N:1]1([C:5]2[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([NH:12][NH:13][C:14](=[O:34])[C@H:15]([CH2:28][CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:16][N:17]([O:20]CC3C=CC=CC=3)[CH:18]=[O:19])[C:6]=2[F:35])[CH2:4][CH2:3][CH2:2]1>CO>[N:1]1([C:5]2[N:10]=[C:9]([CH3:11])[N:8]=[C:7]([NH:12][NH:13][C:14](=[O:34])[C@H:15]([CH2:28][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[CH2:16][N:17]([OH:20])[CH:18]=[O:19])[C:6]=2[F:35])[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 86636927HCID 86636927, compound

Product 1

HCID 58000754[(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamideYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(2R)-3-{2-[6-(1-Azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (3.9 g, 8.0 mmol) was dissolved in 50 mL of MeOH and degassed with argon. 10% Pd/C (400 mg) was added, and the contents were placed under a hydrogen balloon for 4.5 h. The contents were then degassed with argon 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)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (3.1 g, 98%). LCMS: (M+H)+: 395.

Workup

  1. customdegassed with argon
  2. addition10% Pd/C (400 mg) was added
  3. customfor 4.5 h
  4. customThe contents were then degassed with argon
  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-591198adafc34d91af461e364b2c63fc
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

Loading…