Acetic Acid → ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide

HRID 1366402Notes

Reaction equation

HRID 1366402 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[CH2:34][CH:33]=[CH:32][CH2:31]3)[N:26]=[C:25]([CH3:35])[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[CH2:34][CH:33]=[CH:32][CH2:31]3)[N:26]=[C:25]([CH3:35])[N:24]=2)=[O:20])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86636924((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)(tetrahydro-2H-pyran-2-yloxy)formamide

Product 1

HCID 58000536((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamideYield 58.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)(tetrahydro-2H-pyran-2-yloxy)formamide (140 mg) in 4:1 AcOH:water (2 mL) was stirred at room temperature until deprotection was complete. The solvents were removed in vacuo, and the resulting crude product was purified by RP-HPLC to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(2,5-dihydro-1H-pyrrol-1-yl)-5-fluoro-2-methyl-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide (68 mg, 58%). LCMS: (M+H)+: 407.3.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe resulting crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-91642dcf0ca64d7cb32b1ae06849458c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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