1,3-Propanediamine → 1-{4-[(3-Aminopropyl)amino]-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinolin-6-yl}ethanol

HRID 540248Notes

Reaction equation

HRID 540248 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([OH:14])[CH3:13])[CH:10]=2)[N:5]=[C:4]([N:15]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[S:18](=[O:27])(=[O:26])[CH2:17][CH2:16]2)[CH:3]=1.[CH2:28]([NH2:32])[CH2:29][CH2:30][NH2:31]>>[NH2:31][CH2:30][CH2:29][CH2:28][NH:32][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([OH:14])[CH3:13])[CH:10]=2)[N:5]=[C:4]([N:15]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[S:18](=[O:27])(=[O:26])[CH2:17][CH2:16]2)[CH:3]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 712557221-[4-Chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinolin-6-yl]ethanol

Product 1

HCID 866914211-{4-[(3-Aminopropyl)amino]-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinolin-6-yl}ethanolYield 41.2%

Conditions

Temperature
150 °C

Procedure

A mixture of 1-[4-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinolin-6-yl]ethanol (150 mg, 0.387 mmol) and propane-1,3-diamine (55 mg, 0.74 mmol) was heated with stirring in a sealed 0.5 mL of microwave process vial for 1.5 hours at 150° C. under microwave irradiation. The reaction mixture was purified by preparative HPLC and SPE to afford 70.2 mg of the desired product (yield was 41.2%). MS obsd. (ESI+) [(M+H)+] 441, 1H NMR (400 MHz, CD3OD) δ ppm 8.10-8.05 (m, 2 H), 7.86-7.80 (d, J=7.6 Hz, 1 H), 7.78-7.75 (m, 2 H), 7.72-7.62 (t, J=1.2 Hz, 1 H), 7.60-7.50 (t, J=1.2 Hz, 1 H), 5.94 (s, 1 H), 5.30 (s, 2 H), 4.98-4.92 (m, 1 H), 4.58-4.45 (m, 2 H), 3.78-3.70 (t, J=2.8 Hz, 2 H), 3.62-3.53 (t, J=4.4 Hz, 2 H), 3.10-3.02 (t, J=6.8 Hz, 2 H), 2.12-2.02 (m, 2 H), 1.50-1.40 (d, J=6.4 Hz, 3 H).

Workup

  1. temperaturewas heated
  2. customThe reaction mixture was purified by preparative HPLC and SPE

Sources & evidence

ORD record
ord-3bf0cbb604bc49f5945c3e6a534564f6
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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