Pyrrolidine → HCID 10127419, compound

HRID 1296729Notes

Reaction equation

HRID 1296729 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[N:15][N:16]4[C:21]=3[CH:20]=[CH:19][N:18]=[C:17]4SC)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=O.[NH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)=[N:15][N:16]4[C:21]=3[CH:20]=[CH:19][N:18]=[C:17]4[N:42]3[CH2:46][CH2:45][CH2:44][CH2:43]3)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 70297m-Chloroperbenzoic acidHCID 10173307HCID 10173307, compound

Product 1

HCID 10127419HCID 10127419, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-cyclopentyl-4-[2-(4-fluorophenyl)-7-(methylsulfanyl)pyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-amine (24 mg, 0.057 mmol) in dichloromethane (3 mL) was added 3-chloroperoxybenzoic acid (15mg, 0.086 mmol) and the reaction mixture stirred for 1 hour. Pyrrolidine (3 mL) was added and the reaction mixture stirred for 2 hours before being diluted with dichloromethane. The organic phase was washed with saturated sodium bicarbonate, washed with brine, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 5% acetone in dichloromethane to yield N-cyclopentyl-4-[2-(4-fluorophenyl)-7-pyrrolidin-1-ylpyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-amine (15 mg, 59%). 1H NMR (CDCl3): δ 8.05 (d, 1H), 7.65 (d, 1H), 7.60 (dd, 2H), 7.43 (d,1H), 7.10 (t, 2H), 6.27 (d, 1H), 5.05 (d, 1H), 4.29 (m, 1H), 4.09 (t, 4H), 1.99 (m, 6H), 1.45–1.78 (m, 6H). MS m/z 444 (M+1).

Workup

  1. stirringthe reaction mixture stirred for 2 hours
  2. washThe organic phase was washed with saturated sodium bicarbonate
  3. washwashed with brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 5% acetone in dichloromethane

Sources & evidence

ORD record
ord-fb967d6cd4254caa9b58d2666822e1e1
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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