Methylamine → HCID 67270392, compound

HRID 602496Notes

Reaction equation

HRID 602496 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([NH:15][C@@H:16]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:18]([CH2:28]OS(C)(=O)=O)[CH2:17]2)=[O:14])=[N:5]1)([CH3:3])[CH3:2].[CH3:34][NH2:35].C(=O)([O-])O.[Na+]>O1CCCC1>[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([NH:15][C@@H:16]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C@H:18]([CH2:28][NH:35][CH3:34])[CH2:17]2)=[O:14])=[N:5]1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 516892Sodium BicarbonateHCID 86624154HCID 86624154, compound

Product 1

HCID 67270392HCID 67270392, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of tert-butyl (2S,4S)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}-2-{[(methylsulfonyl)oxy]methyl}pyrrolidine-1-carboxylate (197 mg, 0.41 mmol, step 1 of Example 17) and 40% monomethylamine aqueous solution (3 mL) in tetrahydrofuran (2 mL) was stirred at 80° C. for 32 h. After cooling to room temperature, the mixture was added to saturated sodium hydrogencarbonate aqueous solution. The organic phase was extracted with ethyl acetate (10 mL×3). The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was chromatographed on a column of NH gel eluting with n-hexane/ethyl acetate (4:1 to 2:1) to give 66 mg (39%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe organic phase was extracted with ethyl acetate (10 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a column of NH gel
  7. washeluting with n-hexane/ethyl acetate (4:1 to 2:1)

Sources & evidence

ORD record
ord-37e88e618bbb4609bec03bbda5189af6
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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