Trifluoroacetic acid → HCID 59367572, compound

HRID 2079809Notes

Reaction equation

HRID 2079809 reaction equation
C(O)(C(F)(F)F)=O.O1CCCCC1[O:14][NH:15][C:16]([C:18]1[CH:19]=[N:20][C:21]([N:24]2[CH2:27][CH:26]([NH:28][S:29]([C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=3)(=[O:31])=[O:30])[CH2:25]2)=[N:22][CH:23]=1)=[O:17]>C(Cl)Cl.CO>[OH:14][NH:15][C:16]([C:18]1[CH:23]=[N:22][C:21]([N:24]2[CH2:27][CH:26]([NH:28][S:29]([C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=3)(=[O:31])=[O:30])[CH2:25]2)=[N:20][CH:19]=1)=[O:17]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59367688HCID 59367688, compound

Product 1

HCID 59367572HCID 59367572, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

TFA (0.60 ml) was added to a solution of N-(tetrahydro-2H-pyran-2-yloxy) 2-{3-[(2-napthylsulfonyl)amino]azetidin-1-yl}pyrimidine-5-carboxamide (156 mg, 0.32 mmol) in DCM (10 ml) and MeOH (10 ml) at r.t. and the solution stirred at r.t. for 24 h. Further TFA (0.40 ml) was added and stirring continued for a further 18 h. The reaction mixture was concentrated in vacuo and the TFA was removed by azeotroping with DCM to yield a white foam. Trituration in hot DCM (15 ml) and MeOH (1 ml) gave a white precipitate which upon cooling to r.t. was isolated by filtration affording the title compound as a white solid (82 mg, 50%). LCMS purity 100%, m/z 400 [M+H]+, 1H NMR (400 MHz, d5-DMSO) δ: 3.64 (2H, m), 4.12 (2H, t), 4.31 (1H, br s), 7.71-7.76 (2H, m), 7.84 (1H, d), 8.09 (1H, d), 8.18-8.22 (2H, m), 8.49 (1H, s), 8.57 (3H, s), 9.01 (1H, s), 11.07 (1H, s).

Workup

  1. stirringstirring
  2. waitcontinued for a further 18 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe TFA was removed
  5. customby azeotroping with DCM
  6. customto yield a white foam
  7. temperatureupon cooling to r.t.
  8. customwas isolated by filtration

Sources & evidence

ORD record
ord-bf09d80641cb4fc1854d0e21efab4bb2
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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