Methanol → HCID 71255101, compound

HRID 540171Notes

Reaction equation

HRID 540171 reaction equation
Br[C:2]([CH3:31])([CH3:30])[C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=2)[N:9]=[C:8]([N:17]2[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20](=[O:29])(=[O:28])[CH2:19][CH2:18]2)[CH:7]=1)=[O:4].C(N)C.[CH3:35][OH:36]>>[O:28]=[S:20]1(=[O:29])[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH2:23][N:17]([C:8]2[CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([O:36][CH3:35])([CH3:31])[CH3:30])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=3)[N:9]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 71255527HCID 71255527, compound

Product 1

HCID 71255101HCID 71255101, compound

Procedure

To a solution of 2-bromo-N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-2-methylpropanamide (80 mg, 0.159 mmol, prepared in Example 40-2) in methanol (5 mL) was added ethylamine (1 mL), the resulting mixture was heated under reflux overnight. After being cooled to room temperature, the resulting mixture was concentrated in vacuo. The residue was purified by preparative TLC (eluting with 33% ethyl acetate in hexanes) to afford 15 mg of the title compound as a light powder (yield was 21%). MS obsd. (ESI+) [(M+H)+] 454, 1H NMR (400 MHz, CD3OD) δ ppm 7.94-7.89 (m, 3 H), 7.58 (m, 2 H), 7.43-7.39 (m, 3 H), 5.17 (s, 2 H), 4.50 (brs, 2 H), 3.59 (m, 2 H), 3.50 (s, 3 H), 2.46 (s, 3 H), 1.56 (s, 6 H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationthe resulting mixture was concentrated in vacuo
  4. customThe residue was purified by preparative TLC (eluting with 33% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6c1520ce02c140b684a6cea3ccfe39b7
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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