Potassium Carbonate → HCID 71262138, compound

HRID 540234Notes

Reaction equation

HRID 540234 reaction equation
[O:1]=[S:2]1(=[O:37])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][C:24]3([CH2:28][NH:29]C(=O)C(F)(F)F)[CH2:27][O:26][CH2:25]3)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:36])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:29][CH2:28][C:24]1([NH:23][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:36])[CH:19]=3)[N:14]=[C:13]([N:5]3[CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[S:2](=[O:37])(=[O:1])[CH2:3][CH2:4]3)[CH:22]=2)[CH2:25][O:26][CH2:27]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86691416HCID 86691416, compound

Product 1

HCID 71262138HCID 71262138, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[(3-{[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]amino}oxetan-3-yl)methyl]-2,2,2-trifluoroacetamide (190 mg, 0.355 mmol) in methanol (15 mL) was added an aqueous solution of potassium carbonate (197 mg, 1.42 mmol, dissolved in 2 mL of water). After being stirred at room temperature overnight, the resulting mixture was concentrated in vacuo to remove methanol. The residue was diluted with water (5 mL) and extracted with dichloromethane (15 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC to give 23 mg of the desired product as a white solid (yield was 14.8%). MS obsd. (ESI+) [(M+H)+] 439, 1H NMR (400 MHz, CD3OD) δ ppm 7.98-7.96 (m, 1 H), 7.58-7.56 (d, J=6.8 Hz, 1 H), 7.44-7.40 (m, 2 H), 7.32-7.30 (t, 1 H), 7.19 (m, 2 H), 5.99 (s, 1 H), 5.54 (s, 1 H), 4.98-4.97 (d, J=6.0, 4 H), 4.64-4.63 (m, 3 H), 3.51 (s, 2 H), 3.30 (s, 2 H), 2.34 (s, 3 H).

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. customto remove methanol
  3. additionThe residue was diluted with water (5 mL)
  4. extractionextracted with dichloromethane (15 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-693f701cb7084d4583c6997af6e1e2c2
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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