1,3-Propanediamine → N-[6-Methyl-2-(1-oxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinazolin-4-yl]propane-1,3-diamine
Reaction equation
Cl[C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:13])[CH:8]=2)[N:3]=1.[CH2:14]([NH2:18])[CH2:15][CH2:16][NH2:17].[S:19]1(=[O:30])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][NH:22][CH2:21][CH2:20]1>>[CH3:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:22]1[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:19](=[O:30])[CH2:20][CH2:21]1)[N:11]=[C:10]2[NH:17][CH2:16][CH2:15][CH2:14][NH2:18]Participants
4
Procedure
The title compound was prepared in analogy to Example 56-1 in Scheme 23 by using 2,4-dichloro-6-methylquinazoline, propane-1,3-diamine and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1-oxide. MS obsd. (ESI+) [(M+H)+] 396, 1H NMR (400 MHz, CD3OD) δ ppm 7.92 (s, 1 H), 7.81-7.79 (d, J=7.6 Hz, 1 H), 7.74-7.72 (d, J=7.6 Hz, 1 H), 7.64-7.50 (m, 4 H), 5.43-5.39 (d, J=15.6 Hz, 1 H), 5.12-5.05 (m, 1 H), 4.81-4.72 (m, 1 H), 4.53-4.46 (m, 2 H), 3.84-3.82 (m, 2 H), 3.52-3.48 (m, 2 H), 3.31-3.29 (m, 2 H), 2.43 (s, 3 H), 2.17-2.11 (m, 2 H).
Sources & evidence
- ORD record
- ord-650921ba30c14343879a352ea759853c
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871756B2
Reaction notes
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