Sodium Hydroxide → HCID 71262271, compound

HRID 540258Notes

Reaction equation

HRID 540258 reaction equation
FC(F)(F)C([NH:5][CH2:6][C:7]1([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH3:22])[CH:20]=3)[N:15]=[C:14]([N:23]3[CH2:29][C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[S:26](=[O:34])[CH2:25][CH2:24]3)[N:13]=2)[CH2:10][O:9][CH2:8]1)=O.[OH-].[Na+]>C(O)C.O>[NH2:5][CH2:6][C:7]1([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH3:22])[CH:20]=3)[N:15]=[C:14]([N:23]3[CH2:29][C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[S:26](=[O:34])[CH2:25][CH2:24]3)[N:13]=2)[CH2:8][O:9][CH2:10]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86691425HCID 86691425, compound

Product 1

HCID 71262271HCID 71262271, compoundYield 12.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred of 2,2,2-trifluoro-N-[(3-{[6-methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-yl]amino}oxetan-3-yl)methyl]acetamide (70 mg, 0.135 mmol) in ethanol (5 mL) was added an aqueous solution of sodium hydroxide (5 N, 1 mL). After being stirred at room temperature overnight, the resulting mixture was diluted with water (15 mL), and extracted with dichloromethane (15 mL×3). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by preparative HPLC to afford 7 mg of the desired product as a white solid. MS obsd. (ESI+) [(M+H)+] 424, 1H NMR (400 MHz, CD3OD) δ ppm 7.97 (s, 1 H), 7.83-7.78 (m, 2 H), 7.71-7.68 (m, 1 H), 7.61-7.54 (m, 3 H), 5.45 (d, 1 H), 5.15 (brs, 1 H), 4.81-4.74 (m, 5 H), 4.51 (brs, 3 H), 3.54 (brs, 2 H), 2.45 (s, 3 H).

Workup

  1. extractionextracted with dichloromethane (15 mL×3)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-40d3662d7ff149dcb4a503eeedca91df
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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