HCID 86691397, compound → N-[2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-2-methylalaninamide

HRID 540168Notes

Reaction equation

HRID 540168 reaction equation
[N:1]([C:4]([CH3:33])([CH3:32])[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=2)[N:11]=[C:10]([N:19]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[S:22](=[O:31])(=[O:30])[CH2:21][CH2:20]2)[CH:9]=1)=[O:6])=[N+]=[N-]>C(OCC)(=O)C.[Pd]>[O:31]=[S:22]1(=[O:30])[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[CH2:25][N:19]([C:10]2[CH:9]=[C:8]([NH:7][C:5](=[O:6])[C:4]([CH3:33])([CH3:32])[NH2:1])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[N:11]=2)[CH2:20][CH2:21]1

Participants

4

Reactant 1

HCID 86691397HCID 86691397, compound

Product 1

HCID 71254805N-[2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-2-methylalaninamideYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 2-azido-N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-2-methylpropanamide (160 mg, 0.345 mmol) in ethyl acetate (25 mL) was added 10% palladium on carbon (100 mg), the flask was degassed and refilled with hydrogen (repeated for three times). After being stirred at room temperature overnight under a hydrogen atmosphere, the resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography to afford 110 mg of the title compound (yield was 73%). MS obsd. (ESI+) [(M+H)+] 439, 1H NMR (400 MHz, CDCl3) δ ppm 11.05 (s, 1 H), 8.30 (s, 1 H), 8.02 (dd, J=0.8, 7.6 Hz, 1 H), 7.89 (d, J=7.2 Hz, 1 H), 7.59 (d, J=8.8 Hz, 1 H), 7.53 (t, J=7.6 Hz, 1 H), 7.37 (m, 3 H), 5.17 (s, 2 H), 4.6 (brs., 2 H), 3.56 (s, 2 H), 2.48 (s, 3 H), 1.56 (s, 6 H).

Workup

  1. customthe flask was degassed
  2. additionrefilled with hydrogen (repeated for three times)
  3. filtrationthe resulting mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6b5dabad80b4400c80a99452f72620c8
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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