HCID 86636967, compound → HCID 58000702, compound

HRID 1366508Notes

Reaction equation

HRID 1366508 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[CH2:35][CH:34]([N:36]([CH3:38])[CH3:37])[C:33]([CH3:40])([CH3:39])[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[CH2:35][CH:34]([N:36]([CH3:38])[CH3:37])[C:33]([CH3:40])([CH3:39])[CH2:32]2)[N:3]=1

Participants

3

Reactant 1

HCID 86636967HCID 86636967, compound

Product 1

HCID 58000702HCID 58000702, compoundYield 51.3%

Reagents, catalysts & solvents 1

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

Procedure

A solution of [(2R)-3-(2-{2-chloro-6-[4-(dimethylamino)-3,3-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (0.0681 g, 0.117 mmol) in 4:1 HOAc-water (5 mL) was stirred for 56 h and then concentrated in vacuo. A solution of the residue in DCM (100 mL) was washed with sat. aq. NaHCO3 (30 mL), and the organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by Gilson RPLC and crystallized from EtOAc-hexanes to provide [(2R)-3-(2-{2-chloro-6-[4-(dimethylamino)-3,3-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (0.0300 g, 51% yield, mixture of diastereomers) as a white solid. LCMS: (M+H)+: 500.3.

Workup

  1. concentrationconcentrated in vacuo
  2. washA solution of the residue in DCM (100 mL) was washed with sat. aq. NaHCO3 (30 mL)
  3. dry with materialthe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by Gilson RPLC
  7. customcrystallized from EtOAc-hexanes

Sources & evidence

ORD record
ord-f62c4a7e83b74e93b6a8d61c25baaf70
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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