1,3-Propanediamine → HCID 71262216, compound

HRID 540138Notes

Reaction equation

HRID 540138 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[S:16](=[O:25])(=[O:24])[CH2:15][CH2:14]2)[CH:3]=1.[CH2:26]([NH2:30])[CH2:27][CH2:28][NH2:29]>>[NH2:29][CH2:28][CH2:27][CH2:26][NH:30][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([N:13]2[CH2:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[S:16](=[O:25])(=[O:24])[CH2:15][CH2:14]2)[CH:3]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 71255125HCID 71255125, compound

Product 1

HCID 71262216HCID 71262216, compoundYield 27%

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinolin-6-ol (400 mg, 1.067 mmol) and propane-1,3-diamine (158 mg, 2.134 mmol) was heated with stirring for 1.5 hours at 150° C. under microwave irradiation. The reacting mixture was purified by preparative HPLC and SPE to give 118.8 mg of the desired product (yield was 27%). MS obsd. (ESI+)[(M+H)+] 413, 1H NMR (400 MHz, CD3OD) δ ppm 8.10-8.05 (d, J=7.6 Hz, 1 H), 7.85-7.80 (d, J=8 Hz, 1 H), 7.71-7.62 (m, 2 H), 7.60-7.52 (t, J=7.2 Hz, 1 H), 7.40-7.35 (m, 1 H), 7.26-7.20 (dd, J=2.8 Hz, 12.8 Hz, 1 H), 5.91 (s, 1 H), 5.27 (s, 2 H), 4.52-4.42 (m, 2 H), 3.72-3.68 (t, J=2.8 Hz, 2 H), 3.60-3.52 (t, J=6.8 Hz, 2 H), 3.10-3.02 (t, J=7.2 Hz, 2 H), 2.10-2.00 (m, 2 H);

Workup

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

Sources & evidence

ORD record
ord-7114ecea90fb402387965e6220915052
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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