Dimethylformamide → HCID 9997536, compound

HRID 1768151Notes

Reaction equation

HRID 1768151 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)=[CH:10][CH:9]=2)[C:4]1=[O:23].C(N(C(C)C)C(C)C)C.C[N:34](C)[CH:35]=[O:36]>>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([N:5]2[CH2:6][CH2:7][C@@H:3]([NH:2][C:35]([NH2:34])=[O:36])[C:4]2=[O:23])=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 69491090HCID 69491090, compound

Product 1

HCID 9997536HCID 9997536, compound

Procedure

A solution of 250 mg (0.7 mmol) of (R)-3-amino-1-[4-(3-fluoro-benzyloxy)-phenyl]-pyrrolidin-2-one hydrochloride and 294 mg (2.2 mmol) of N-ethyl-diisopropylamine in 2 ml of N,N-dimethylformamide is cooled to 0° C. and treated with 267 mg (2.2 mol) of trimethylisocyanate. The reaction mixture is left to warm to RT and stirring is continued for 2 days. For the working-up, the suspension is evaporated under reduced pressure. The crude product is triturated in water, then the recovered solid material triturated a second time in a mixture of ethyl acetate and a saturated solution of sodium hydrogencarbonate. The remaining solid is collected on a filter funnel to give, after drying under high vacuum, 155 mg (61% of theory) of (R)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-urea as a white solid; MS: m/e=344 (M+H)+.

Workup

  1. waitThe reaction mixture is left
  2. customthe suspension is evaporated under reduced pressure
  3. customThe crude product is triturated in water
  4. customthe recovered solid material triturated a second time
  5. additionin a mixture of ethyl acetate
  6. customThe remaining solid is collected on a filter funnel
  7. customto give
  8. dry with materialafter drying under high vacuum, 155 mg (61% of theory) of (R)-{1-[4-(3-fluoro-benzyloxy)-phenyl]-2-oxo-pyrrolidin-3-yl}-urea as a white solid

Sources & evidence

ORD record
ord-bd15441a52cb408dab5bd8d5a21f49c5
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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