Trifluoroacetic acid → HCID 56832815, compound

HRID 2401901Notes

Reaction equation

HRID 2401901 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][C:6]1[N:7]=[C:8]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[S:9][C:10]=1[C:11]([NH:13][O:14]C1CCCCO1)=[O:12].FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][C:6]1[N:7]=[C:8]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[S:9][C:10]=1[C:11]([NH:13][OH:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86667484HCID 86667484, compound

Product 1

HCID 56832815HCID 56832815, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3,4-dichlorobenzyl)-2-(morpholin-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,3-thiazole-5-carboxamide (153 mg, 0.324 mmol) in methylene chloride (1.50 mL) was added trifluoroacetic Acid (1.50 mL, 19.5 mmol). The reaction was stirred at rt for 12 hrs. The resulting solution was concentrated and distributed between NaHCO3(aq) saturated solution and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (×2). The combined org layer was washed with water, dried, and concentrated. Purification on a silica gel column (gradient elution, 0-8% MeOH/CH2Cl2) provided 4-(3,4-dichlorobenzyl)-N-hydroxy-2-(morpholin-4-yl)-1,3-thiazole-5-carboxamide as a yellow solid (53 mg, 42.1% yield). LCMS: (AA) ES+ 388, 390, 392; 1H NMR (400 MHz, MeOD) δ 7.47-7.41 (d, J=1.8 Hz, 1H), 7.38-7.29 (d, J=8.3 Hz, 1H), 7.25-7.14 (dd, J=8.3, 1.9 Hz, 1H), 4.28-4.21 (s, 2H), 3.79-3.71 (t, J=4.9 Hz, 4H), 3.50-3.43 (t, J=4.9 Hz, 4H), 3.33-3.27 (t, J=1.6 Hz, 1H).

Workup

  1. concentrationThe resulting solution was concentrated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (×2)
  3. washThe combined org layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customPurification
  7. washon a silica gel column (gradient elution, 0-8% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ef61f7fbd68e432f9e7133b82d226119
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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