[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-6-[(7S)-7-hydroxy-5-azaspiro[2.4]hept-5-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide → ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-6-(7-hydroxy-5-azaspiro[2.4]hept-5-yl)-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide

HRID 1366498Notes

Reaction equation

HRID 1366498 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:19]([NH:21][NH:22][C:23]2[C:28]([F:29])=[C:27]([N:30]3[CH2:36][C@@H:35]([OH:37])[C:32]4([CH2:34][CH2:33]4)[CH2:31]3)[N:26]=[C:25]([CH3:38])[N:24]=2)=[O:20])[CH2:8][N:9]([O:12]C2CCCCO2)[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>CC(O)=O.O>[CH:1]1([CH2:6][C@@H:7]([C:19]([NH:21][NH:22][C:23]2[C:28]([F:29])=[C:27]([N:30]3[CH2:36][CH:35]([OH:37])[C:32]4([CH2:34][CH2:33]4)[CH2:31]3)[N:26]=[C:25]([CH3:38])[N:24]=2)=[O:20])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 86636963[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-6-[(7S)-7-hydroxy-5-azaspiro[2.4]hept-5-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Product 1

HCID 58000545((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-6-(7-hydroxy-5-azaspiro[2.4]hept-5-yl)-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamideYield 27.5%

Reagents, catalysts & solvents 1

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

Procedure

[(2R)-2-(Cyclopentylmethyl)-3-(2-{5-fluoro-6-[(7S)-7-hydroxy-5-azaspiro[2.4]hept-5-yl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (91 mg, 0.202 mmol) was dissolved in a mixture of AcOH/H2O (10 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 was purified by RP-HPLC to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-6-(7-hydroxy-5-azaspiro[2.4]hept-5-yl)-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide (25 mg, 27%). LCMS: (M+H)+: 451.2.

Workup

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

Sources & evidence

ORD record
ord-3e7d696b6f474bc1b2a07898eb21a58f
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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