Cyclopentylamine → HCID 178428238, compound

HRID 499063Notes

Reaction equation

HRID 499063 reaction equation
[N:1]1([C:5]2[CH:10]=[C:9]([NH:11][C:12]3[NH:13][N:14]=[C:15]([CH3:17])[CH:16]=3)[N:8]=[C:7]([S:18][C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.[CH:28]1([NH2:33])[CH2:32][CH2:31][CH2:30][CH2:29]1.F[B-](F)(F)F.CN(C)C(O)=[N+](C)C.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[N:1]1([C:5]2[CH:10]=[C:9]([NH:11][C:12]3[NH:13][N:14]=[C:15]([CH3:17])[CH:16]=3)[N:8]=[C:7]([S:18][C:19]3[CH:27]=[CH:26][C:22]([C:23]([NH:33][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:24])=[CH:21][CH:20]=3)[N:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 2906CyclopentylamineHCID 81531DiisopropylethylamineHCID 13074157Tetramethyluronium tetrafluoroborateHCID 178428239HCID 178428239, compound

Product 1

HCID 178428238HCID 178428238, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 25 ml round bottom flask was charged with 4-[4-azetidin-1-yl-6-(5-methyl-2H-pyrazol-3-ylamino)-pyrimidin-2-ylsulfanyl]-benzoic acid (200 mg, 0.48 mmol), cyclopentyl amine (85 mg, 1 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3, -tetramethyluroniumtetrafluoroborate (321 mg, 1 mmol), diisopropylethylamine (0.34 ml, 2 mmol) in dimethylformamide (5 ml), under nitrogen. The reaction mixture was stirred at room temperature for 18 hours and then was diluted with ethyl acetate (40 ml), washed with a saturated sodium hydrogen carbonate aqueous solution (40 ml) and brine (40 ml). The organic was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated in dichloromethane to afford the title compound. 1H NMR (DMSO-d6): 1.60-1.65 (4H, m), 1.70-1.80 (2H, m), 1.95-2.10 (5H, m), 2.20-2.30 (2H, m), 3.90-4.00 (4H, s), 4.30-4.35 (1H, m), 5.35-5.40 (1H, s), 7.70-7.75 (2H, d), 8.00-8.05 (2H, d), 8.45-8.50 (1H, d), 9.3 (1H, s). MS (ES+): 450.

Workup

  1. washwashed with a saturated sodium hydrogen carbonate aqueous solution (40 ml) and brine (40 ml)
  2. dry with materialThe organic was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated in dichloromethane

Sources & evidence

ORD record
ord-e8007b34f6b244fe868057f148da715b
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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