Trifluoroacetic acid → HCID 54596589, compound

HRID 1429544Notes

Reaction equation

HRID 1429544 reaction equation
[P:1]([O:50]CC[Si](C)(C)C)([O:43]CC[Si](C)(C)C)([O:3][C:4]([CH3:42])([CH2:6][CH2:7][S:8]([N:11]1[CH2:16][CH2:15][C:14]([C:17]2[CH:41]=[CH:40][C:20]3[N:21]=[C:22]([O:24][CH:25]4[CH2:30][CH2:29][N:28]([C:31]5[N:36]=[CH:35][C:34]([CH2:37][CH2:38][CH3:39])=[CH:33][N:32]=5)[CH2:27][CH2:26]4)[S:23][C:19]=3[CH:18]=2)=[CH:13][CH2:12]1)(=[O:10])=[O:9])[CH3:5])=[O:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[P:1]([OH:43])([OH:50])([O:3][C:4]([CH3:42])([CH2:6][CH2:7][S:8]([N:11]1[CH2:16][CH2:15][C:14]([C:17]2[CH:41]=[CH:40][C:20]3[N:21]=[C:22]([O:24][CH:25]4[CH2:30][CH2:29][N:28]([C:31]5[N:32]=[CH:33][C:34]([CH2:37][CH2:38][CH3:39])=[CH:35][N:36]=5)[CH2:27][CH2:26]4)[S:23][C:19]=3[CH:18]=2)=[CH:13][CH2:12]1)(=[O:9])=[O:10])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 71269983HCID 71269983, compound

Product 1

HCID 54596589HCID 54596589, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-(4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butan-2-yl bis(2-(trimethylsilyl)ethyl) phosphate (85 mg, 0.098 mmol) in CH2Cl2 (511 μl) at 0° C. was added TFA (51.1 μl, 0.663 mmol). The mixture was stirred and gradually warmed to rt for 4 h. It was cooled to 0° C. and an aqueous solution of NaHCO3 (saturated, 0.5 mL) was added. The solvent was removed and the solid was collected via filtering. The solid was rinsed with cold H2O and ether. It was dried under vacuum to yield 2-methyl-4-(4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)butan-2-yl dihydrogen phosphate (53 mg, 0.079 mmol, 80% yield) as a white solid. 1H NMR (500 MHz, DMSO) δ 8.17 (s, 2H), 7.90 (s, 1H), 7.56 (d, J=8.5 Hz, 1H), 7.43 (d, J=8.6 Hz, 1H), 6.14 (s, 1H), 5.33 (s, 1H), 4.12 (d, J=13.6 Hz, 2H), 3.90 (s, 2H), 3.47 (dd, J=24.6, 14.8 Hz, 4H), 2.53 (s, 4H), 2.35-2.24 (m, 3H), 2.06 (m, 2H), 1.90 (m, 2H), 1.69 (m, 2H), 1.46 (dd, J=14.7, 7.4 Hz, 2H), 1.20 (s, 6H), 0.81 (t, J=7.3 Hz, 3H). LCMS (m/z)=665 (M+H)+.

Workup

  1. temperatureIt was cooled to 0° C.
  2. customThe solvent was removed
  3. customthe solid was collected
  4. filtrationvia filtering
  5. washThe solid was rinsed with cold H2O and ether
  6. customIt was dried under vacuum

Sources & evidence

ORD record
ord-01e3a9c336c249e786cd7b2b91ed7da5
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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