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

HRID 1366492Notes

Reaction equation

HRID 1366492 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][NH:17][C:18](=[O:37])[C@H:19]([CH2:31][CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:20][N:21]([O:24]C3CCCCO3)[CH:22]=[O:23])[C:10]=2[F:38])[N:6]=1.CC(O)=O>O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][NH:8][C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:16][NH:17][C:18](=[O:37])[C@H:19]([CH2:31][CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:20][N:21]([OH:24])[CH:22]=[O:23])[C:10]=2[F:38])[N:6]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86636961[(2R)-3-[2-(6-{[(2-amino-1,3-thiazol-4-yl)methyl]amino}-5-fluoro-2-methyl-4-pyrimidinyl)hydrazino]-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Product 1

HCID 86636962[(2R)-3-[2-(6-{[(2-amino-1,3-thiazol-4-yl)methyl]amino}-5-fluoro-2-methyl-4-pyrimidinyl)hydrazino]-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamideYield 19.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[(2R)-3-[2-(6-{[(2-Amino-1,3-thiazol-4-yl)methyl]amino}-5-fluoro-2-methyl-4-pyrimidinyl)hydrazino]-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (114 mg, 0.2 mmol) in 4:1 AcOH:water (5 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-(6-{[(2-amino-1,3-thiazol-4-yl)methyl]amino}-5-fluoro-2-methyl-4-pyrimidinyl)hydrazino]-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (18 mg, 18%). LCMS: (M+H)+: 481.2.

Workup

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

Sources & evidence

ORD record
ord-6cca736943184cfda5a00c093a70e5ff
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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