Trifluoroacetic acid → HCID 59367575, compound

HRID 2079805Notes

Reaction equation

HRID 2079805 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C:11]1[CH:12]=[N:13][C:14]([NH:17][CH:18]2[CH:23]3[CH:19]2[CH2:20][N:21]([S:24]([C:27]2[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=2)(=[O:26])=[O:25])[CH2:22]3)=[N:15][CH:16]=1)=[O:10].C(O)(C(F)(F)F)=O>CO.C(Cl)Cl>[OH:7][NH:8][C:9]([C:11]1[CH:16]=[N:15][C:14]([NH:17][CH:18]2[CH:23]3[CH:19]2[CH2:20][N:21]([S:24]([C:27]2[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=2)(=[O:26])=[O:25])[CH2:22]3)=[N:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59367593HCID 59367593, compound

Product 1

HCID 59367575HCID 59367575, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(tetrahydro-2H-pyran-2-yloxy) 2-{[3-(2-napthylsulphonyl)-3-azabicyclo[3.1.0]hex-6-yl]amino}pyrimidine-5-carboxamide (110 mg, 0.21 mmol) in MeOH (15 ml) and DCM (15 ml), was added TFA (1.5 ml) at r.t. The mixture was stirred for 8 h before removal of solvent in vacuo. Excess TFA was removed by re-dissolving in DCM (5 ml×2) and concentration to dryness under reduced pressure. Purification by preparative HPLC gave the title compound as a white solid (25.1 mg, 21%). LCMS purity 100%, m/z 426 [M+H]+, 1H NMR (400 MHz, d6-DMSO) δ: 1.15 (2H, s), 2.55 (1H, s), 3.20 (2H, d), 3.65 (2H, d), 7.65 (2H, m), 7.75 (1H, d), 7.90 (1H, m), 8.15-8.30 (3H, m), 8.50 (1H, s), 8.65 (2H, s).

Workup

  1. customExcess TFA was removed
  2. dissolutionby re-dissolving in DCM (5 ml×2)
  3. concentrationconcentration to dryness under reduced pressure
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-f7b7c8c613ad43d9acca845f3f87109d
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

Loading…