Acetic Acid → HCID 58000741, compound

HRID 1366395Notes

Reaction equation

HRID 1366395 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[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][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[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[N:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86636920[(2R)-3-{2-[2-chloro-5-fluoro-6-(4-methyl-1-piperazinyl)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy) formamide

Product 1

HCID 58000741HCID 58000741, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of [(2R)-3-{2-[2-chloro-5-fluoro-6-(4-methyl-1-piperazinyl)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (30 mg) in 4:1 AcOH:water (4 mL) was stirred at room temperature overnight. The solvents were removed in vacuo, and the resulting crude product was purified by RP-HPLC to provide [(2R)-3-{2-[2-chloro-5-fluoro-6-(4-methyl-1-piperazinyl)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (12 mg, 47%). LCMS: (M+H)+: 458.3.

Workup

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

Sources & evidence

ORD record
ord-b8bc5fbe82814f16a02ce08b29e703a2
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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