HCID 86636932, compound → HCID 58000621, compound

HRID 1366423Notes

Reaction equation

HRID 1366423 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[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]3)[N:26]=[C:25]([S:37][CH3:38])[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>C(O)(=O)C.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][CH2:32][N:33]([CH3:36])[CH2:34][CH2:35]3)[N:26]=[C:25]([S:37][CH3:38])[N:24]=2)=[O:20])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86636932HCID 86636932, compound

Product 1

HCID 58000621HCID 58000621, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

((2R)-2-(Cyclopentylmethyl)-3-{2-[5-fluoro-6-(4-methyl-1-piperazinyl)-2-(methylthio)-4-pyrimidinyl]hydrazino}-3-oxopropyl)(tetrahydro-2H-pyran-2-yloxy)formamide (2.5 g, 22.58 mmol) was dissolved in acetic acid/water (4:1, 1 L) and stirred at RT for 3 days. The reaction mixture was concentrated to dryness and co-evaporated with toluene (20 mL) followed by methanol (50 mL)/triethylamine (20 mL). The residue was dissolved in methanol (120 mL) and triethylamine (20 mL) and purified by Gilson HPLC (10-95% acetonitrile/water, 8 min gradient time) to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[5-fluoro-6-(4-methyl-1-piperazinyl)-2-(methylthio)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide as a reddish foamy solid (6.90 g, 65.1%). LCMS: (M+H)+: 470.2.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness and co-evaporated with toluene (20 mL)
  2. dissolutionThe residue was dissolved in methanol (120 mL)
  3. customtriethylamine (20 mL) and purified by Gilson HPLC (10-95% acetonitrile/water, 8 min gradient time)

Sources & evidence

ORD record
ord-e64023fe5ca14690ae0ce5c3fd709de3
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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