[(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide → [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentyl methyl)-3-oxopropyl]hydroxyformamide

HRID 1366484Notes

Reaction equation

HRID 1366484 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:10](=[O:29])[C@H:11]([CH2:23][CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12][N:13]([O:16]C2CCCCO2)[CH:14]=[O:15])[C:5]([F:30])=[C:4]([N:31]2[CH2:35][C@@H:34]([OH:36])[C:33]([CH3:38])([CH3:37])[CH2:32]2)[N:3]=1>CC(O)=O.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][NH:9][C:10](=[O:29])[C@H:11]([CH2:23][CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:12][N:13]([OH:16])[CH:14]=[O:15])[C:5]([F:30])=[C:4]([N:31]2[CH2:35][C@@H:34]([OH:36])[C:33]([CH3:38])([CH3:37])[CH2:32]2)[N:3]=1

Participants

3

Reactant 1

HCID 86636956[(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Product 1

HCID 58000541[(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentyl methyl)-3-oxopropyl]hydroxyformamideYield 63%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (0.1294 g, 0.232 mmol) in 4:1 HOAc-water (5 mL) was heated at 30° C. and stirred overnight. The solution was cooled to room temperature, concentrated in vacuo, and purified directly by Gilson RPLC to give [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (69.1 mg, 63% yield) as a yellow solid. LCMS: (M+H)+: 473.2.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified directly by Gilson RPLC

Sources & evidence

ORD record
ord-9ba66309a519439cac4f7011c93f85b8
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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