HCID 86637010, compound → HCID 58000731, compound

HRID 1366629Notes

Reaction equation

HRID 1366629 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]([NH:31][CH2:32][C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)[N:3]=1>C(O)(=O)C.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]([NH:31][CH2:32][C:33]2[CH:37]=[CH:36][S:35][CH:34]=2)[N:3]=1

Participants

4

Reactant 1

HCID 86637010HCID 86637010, compound

Product 1

HCID 58000731HCID 58000731, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

[(2R)-3-(2-{2-Chloro-5-fluoro-6-[(3-thienylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (0.7045 g, 1.272 mmol) was dissolved in acetic acid (8 mL) and water (2 mL). The reaction mixture was stirred overnight. The volatiles were evaporated, and the resulting residue was purified by RP-HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[(3-thienylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide as a beige solid (0.2284 g, 38%). LCMS: (M+H)+=471.0.

Workup

  1. customThe volatiles were evaporated
  2. customthe resulting residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-bba29a4207fc48a7bb285740a8b44314
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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