Acetic Acid → [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide

HRID 1366590Notes

Reaction equation

HRID 1366590 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[CH2:33][C:32]([CH3:39])([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)[CH2:31]3)[N:26]=[C:25]([CH3:40])[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[CH2:31][C:32]([CH3:39])([N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)[CH2:33]3)[N:26]=[C:25]([CH3:40])[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

4

Reactant 2

HCID 176Acetic AcidHCID 86636996[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}hydrazino)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Product 1

HCID 58000653[(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamideYield 64.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}hydrazino)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (118 mg) in 4:1 AcOH:water (20 mL) was stirred at room temperature for 3 days. The solvents were removed in vacuo, and the resulting crude product was purified by RP-HPLC to provide [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-2-methyl-6-[3-methyl-3-(1-pyrrolidinyl)-1-azetidinyl]-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide (65 mg, 64%). LCMS: (M+H)+: 478.1.

Workup

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

Sources & evidence

ORD record
ord-473d3691acf04efab7dbd6866ca9b7dd
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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