HCID 86637001, compound → [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide

HRID 1366604Notes

Reaction equation

HRID 1366604 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[S:34][CH:35]=[CH:36][N:37]=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[S:34][CH:35]=[CH:36][N:37]=2)[N:3]=1

Participants

4

Reactant 1

HCID 86637001HCID 86637001, compound

Product 1

HCID 58000533[(2R)-3-(2-{2-chloro-5-fluoro-6-[(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamideYield 58%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

[(2R)-3-(2-{2-Chloro-5-fluoro-6-[(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (0.3031 g, 0.5461 mmol) was dissolved in acetic acid (8 mL) and water (2 mL). This reaction mixture was stirred overnight. The volatiles were evaporated and reaction mixture was purified by RP-HPLC to provide [(2R)-3-(2-{2-chloro-5-fluoro-6-[(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide as a white solid (0.1484 g, 58%). LCMS: (M+H)+=472.0.

Workup

  1. customThe volatiles were evaporated
  2. customreaction mixture
  3. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-5aaa2bf8698642e5a043f2ade4596be0
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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