1,3-Propanediamine → N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-7-methylquinolin-4-yl]propane-1,3-diamine

HRID 540112Notes

Reaction equation

HRID 540112 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][NH2:4].Cl[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH3:17])[N:10]=[C:9]([N:18]2[CH2:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[S:21](=[O:30])(=[O:29])[CH2:20][CH2:19]2)[CH:8]=1.ClC1C2C(=CC(C)=CC=2)N=C(N2CC3C=CC=CC=3S(=O)(=O)CC2)C=1.ClC1C2C(=CC=C(OC(F)(F)F)C=2)N=C(N2CC3C=CC=CC=3S(=O)(=O)CC2)C=1.ClC1C=C(Cl)C2C(=CC=CC=2C)N=1.ClC1C=C(Cl)C2C(=CC(C)=CC=2)N=1>>[O:29]=[S:21]1(=[O:30])[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[CH2:24][N:18]([C:9]2[CH:8]=[C:7]([NH:4][CH2:3][CH2:2][CH2:1][NH2:5])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH3:17])[N:10]=2)[CH2:19][CH2:20]1.[O:29]=[S:21]1(=[O:30])[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[CH2:24][N:18]([C:9]2[CH:8]=[C:7]([NH:4][CH2:3][CH2:2][CH2:1][NH2:5])[C:12]3[C:11](=[CH:16][C:15]([CH3:17])=[CH:14][CH:13]=3)[N:10]=2)[CH2:19][CH2:20]1

Participants

8

Reactant 6

HCID 4281,3-Propanediamine2×HCID 34829982,4-Dichloro-5-methylquinolineHCID 586456282,4-Dichloro-7-methylquinolineHCID 712545694-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxideHCID 897134284-(4-Chloro-5-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxideHCID 897137104-(4-Chloro-7-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

Product 2

HCID 89713052N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-7-methylquinolin-4-yl]propane-1,3-diamineHCID 89713301N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-5-methylquinolin-4-yl]propane-1,3-diamine

Procedure

A mixture of the title compound prepared in analogy to Example 17-1 by using propane-1,3-diamine and a mixture of 4-(4-chloro-5-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide and 4-(4-chloro-7-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (prepared in analogy to 4-(4-chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide in Example 17-1 by using a mixture of 2,4-dichloro-5-methylquinoline and 2,4-dichloro-7-methylquinoline and propane-1,3-diamine) was purified by preparative HPLC and SPE to give the pure title compounds N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-5-methylquinolin-4-yl]propane-1,3-diamine and N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-7-methylquinolin-4-yl]propane-1,3-diamine.

Workup

  1. customprepared in analogy to Example 17-1
  2. customwas purified by preparative HPLC and SPE

Sources & evidence

ORD record
ord-488b6db5bf9c46a6b0f57f2200255455
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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