Potassium Hydroxide → HCID 71255147, compound

HRID 540228Notes

Reaction equation

HRID 540228 reaction equation
[NH2:1][C:2]1([CH2:6][NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[N:11]=[C:10]([N:19]3[CH2:25][C:24]4[CH:26]=[C:27]([O:30]C)[CH:28]=[CH:29][C:23]=4[S:22](=[O:33])(=[O:32])[CH2:21][CH2:20]3)[CH:9]=2)[CH2:5][O:4][CH2:3]1.[OH-].[K+]>CS(C)=O>[NH2:1][C:2]1([CH2:6][NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[N:11]=[C:10]([N:19]3[CH2:25][C:24]4[CH:26]=[C:27]([OH:30])[CH:28]=[CH:29][C:23]=4[S:22](=[O:32])(=[O:33])[CH2:21][CH2:20]3)[CH:9]=2)[CH2:3][O:4][CH2:5]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 71255111HCID 71255111, compound

Product 1

HCID 71255147HCID 71255147, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-[(3-aminooxetan-3-yl)methyl]-2-(7-methoxy-1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine (20 mg, 0.044 mmol, prepared in analogy to Example 1-5), potassium hydroxide (24 mg, 0.44 mmol) in dimethylsulfoxide (2 mL) was heated with stirring in a sealed 5 mL of microwave process via for 20 minutes at 100° C. under microwave irradiation. The resulting mixture was purified by preparative HPLC to afford 6 mg of the product (yield was 30%). MS obsd. (ESI+) [(M+H)+] 455, 1HNMR (400 MHz, CD3OD) δ ppm 7.77 (d, J=8.59 Hz, 1 H), 7.67 (s, 1 H), 7.45 (d, J=8.59 Hz, 1 H), 7.31 (dd, J=8.46, 1.64 Hz, 1 H), 7.18 (d, J=2.53 Hz, 1 H), 6.72 (dd, J=8.59, 2.27 Hz, 1 H), 6.19 (s, 1 H), 5.03 (s, 2 H), 4.68 (d, J=6.57 Hz, 2 H), 4.61 (d, J=6.57 Hz, 2 H), 3.66 (s, 2 H), 3.50 (brs, 2 H), 3.30 (m, 2 H), 2.43 (s, 3 H).

Workup

  1. temperaturewas heated
  2. customThe resulting mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-549a4efce8514b7e9fdff144c698c50d
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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