[(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide → [(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide

HRID 1366392Notes

Reaction equation

HRID 1366392 reaction equation
[N:1]1([C:5]2[N:10]=[C:9]([S:11][CH3:12])[N:8]=[C:7]([NH:13][NH:14][C:15](=[O:34])[C@H:16]([CH2:28][CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:17][N:18]([O:21]C3CCCCO3)[CH:19]=[O:20])[C:6]=2[F:35])[CH2:4][CH2:3][CH2:2]1>CC(O)=O.O>[N:1]1([C:5]2[N:10]=[C:9]([S:11][CH3:12])[N:8]=[C:7]([NH:13][NH:14][C:15](=[O:34])[C@H:16]([CH2:28][CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33]3)[CH2:17][N:18]([OH:21])[CH:19]=[O:20])[C:6]=2[F:35])[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 86636918[(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Product 1

HCID 58000553[(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamideYield 45.1%

Reagents, catalysts & solvents 1

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

Procedure

[(2R)-3-{2-[6-(1-Azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (68 mg, 0.13 mmol) was dissolved in a mixture of AcOH/H2O (20 mL, 4:1) and stirred at RT until LCMS indicated completion of the deprotection (overnight). The reaction mixture was concentrated to dryness under vacuum and purified by RP-HPLC to provide [(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (25 mg, 44%). LCMS: (M+H)+: 427.2.

Workup

  1. customcompletion of the deprotection (overnight)
  2. concentrationThe reaction mixture was concentrated to dryness under vacuum
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-847abcbd46e9420983d4d1d356fc1fce
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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