Trifluoroacetic acid → HCID 67261286, compound

HRID 1040120Notes

Reaction equation

HRID 1040120 reaction equation
[OH:1][C:2]1([C:6]2[S:7][C:8]([C:11]3[CH:12]=[C:13]([NH:18][C:19]4[N:24]=[C:23]([O:25][CH:26]5[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]5)[CH:22]=[CH:21][N:20]=4)[CH:14]=[C:15]([CH3:17])[CH:16]=3)=[CH:9][N:10]=2)[CH2:5][CH2:4][CH2:3]1.FC(F)(F)C(O)=O>ClCCl>[NH:28]1[CH2:27][CH:26]([O:25][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([NH:18][C:13]3[CH:12]=[C:11]([C:8]4[S:7][C:6]([C:2]5([OH:1])[CH2:5][CH2:4][CH2:3]5)=[N:10][CH:9]=4)[CH:16]=[C:15]([CH3:17])[CH:14]=3)[N:24]=2)[CH2:29]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67432382HCID 67432382, compound

Product 1

HCID 67261286HCID 67261286, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step 2 (200 mg, 0.39 mmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (0.49 mL). The mixture was stirred for 1 h at room temperature and then concentrated under reduced pressure. The resulting residue was taken up in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 1-[5-(3-{[4-(azetidin-3-yloxy)pyrimidin-2-yl]amino}-5-methylphenyl)-1,3-thiazol-2-yl]cyclobutanol (158 mg, 0.39 mmol, 98%) as a pale-yellow foam. MS ESI: [M+H]+ m/z 409.8. 1H NMR (500 MHz, DMSO-d6) δ 9.53 (s, 1H), 8.23 (d, J=5.6, 1H), 7.98 (s, 1H), 7.80 (s, 1H), 7.52 (s, 1H), 7.09 (s, 1H), 6.64-6.52 (m, 1H), 6.29 (d, J=5.6, 1H), 5.55-5.36 (m, 1H), 3.76 (dd, J=6.7, 9.7, 2H), 3.58-3.45 (m, 2H), 2.56-2.49 (m, 3H), 2.37-2.20 (m, 5H), 1.87 (dt, J=7.0, 10.0, 2H). rhSYK activity=+++

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf654e5afb7047659d7ba0430111d07a
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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