Trifluoroacetic acid → HCID 67261286, compound

HRID 410628Notes

Reaction equation

HRID 410628 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-a9097bedb3b3448f94177378b5e0712e
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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