Trifluoroacetic acid → HCID 71075277, compound

HRID 1028099Notes

Reaction equation

HRID 1028099 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([N:24]([C:32]2[N:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][N:33]=2)C(=O)OC(C)(C)C)[CH:8]=[C:9]([C:11]2[S:15][C:14]([N:16]3[CH2:22][CH2:21][CH2:20][NH:19][C:18](=[O:23])[CH2:17]3)=[N:13][CH:12]=2)[CH:10]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[O:23]=[C:18]1[NH:19][CH2:20][CH2:21][CH2:22][N:16]([C:14]2[S:15][C:11]([C:9]3[CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=[C:7]([NH:24][C:32]4[N:37]=[C:36]([C:38]([F:39])([F:41])[F:40])[CH:35]=[CH:34][N:33]=4)[CH:8]=3)=[CH:12][N:13]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67262174HCID 67262174, compound

Product 1

HCID 71075277HCID 71075277, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl {3-(acetylamino)-5-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]phenyl}[4-(trifluoromethyl)pyrimidin-2-yl]carbamate (79 mg, 0.134 mmol) in dichloromethane (1 mL) at room temperatrue, under nitrogen, was added trifluoroacetic acid (1 mL, 13 mmol). The mixture was stirred at room temperature for 1 h and concentrated to dryness. The residue was partitioned between ethyl acetate and 5% aqueous sodium bicarbonate. The solid product precipitated in the two phases. The organic layer was concentrated to dryness and the residue was transferred into the aqueous with a small amount of EtOH. The resulting aqueous suspension was filtered, the solids collected, and washed with water, a small amount of ethanol, then hexane, and dried to afford 48 mg (0.098 mmol, 73% yield) of N-(3-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)acetamide as an off-white solid. MS APCI: [M+H]+ m/z 492.1. 1H NMR (400 MHz, d6-dmso): δ 10.25 (s, 1H); 9.98 (s, 1H); 8.82 (d, J=4.9 Hz, 1H); 7.75 (m, 2H); 7.61 (br t, J=5.0 Hz, 1H); 7.43-7.37 (m, 2H); 7.28 (d, J=4.9 Hz, 1H); 4.19 (s, 2H); 3.81 (m, 2H); 3.24 (m, 2H); 2.05 (s, 3H); 1.80 (m, 2H). rhSyk=+++.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between ethyl acetate and 5% aqueous sodium bicarbonate
  3. customThe solid product precipitated in the two phases
  4. concentrationThe organic layer was concentrated to dryness
  5. filtrationThe resulting aqueous suspension was filtered
  6. customthe solids collected
  7. washwashed with water
  8. dry with materiala small amount of ethanol, then hexane, and dried

Sources & evidence

ORD record
ord-b3eb2eb92844484b90c2e11fb923dd70
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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