Hydrochloric Acid → HCID 71255135, compound

HRID 540157Notes

Reaction equation

HRID 540157 reaction equation
[O:1]=[S:2]1(=[O:40])[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][CH2:24][CH:25]3[CH2:29][O:28]C(C)(C)[N:26]3C(OC(C)(C)C)=O)[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:39])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.Cl>C(OCC)(=O)C>[NH2:26][C@@H:25]([CH2:24][NH:23][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:39])[CH:19]=2)[N:14]=[C:13]([N:5]2[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:2](=[O:40])(=[O:1])[CH2:3][CH2:4]2)[CH:22]=1)[CH2:29][OH:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71255485HCID 71255485, compound

Product 1

HCID 71255135HCID 71255135, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-({[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]amino}methyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (251 mg) and a solution of hydrochloride in ethyl acetate (13 mL, 4 N) was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. The residue was dissolved in water, and basified with a saturated aqueous solution of sodium bicarbonate to about pH 9, and extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo. The residue was purified by preparative HPLC to give 74.6 mg of the desired product as a white solid. MS obsd. (ESI+) [(M+H)+] 427, 1H NMR (400 MHz, CD3OD) δ ppm 8.04 (dd, J=1.2, 8.0 Hz, 1 H), 7.98 (d, J=7.2 Hz, 1 H), 7.86 (s, 1 H), 7.72-7.66 (m, 2 H), 7.55-7.46 (m, 2 H), 6.20 (s, 1 H), 5.31 (s, 2 H), 4.57 (s, 2 H), 3.93-3.62 (m, 7 H), 2.47 (s, 3 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate (20 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-8cc841651d9b4ec39ac636ad4353f832
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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