Taurine → 2-(4-(3-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamoyl)piperazin-1-yl)ethanesulfonic acid

HRID 2175269Notes

Reaction equation

HRID 2175269 reaction equation
NC1C=C(C=CC=1)CN1N=NC(C2C=CC=[C:17]3[C:12]=2C[CH2:14][CH2:15][N:16]3[C:21](=[O:34])CCCOC2C=CC=C(C)C=2C)=N1.[NH2:38][CH2:39][C:40]1[CH:41]=[C:42]([C:46]2[CH:55]=[CH:54][CH:53]=[C:52]3[C:47]=2[CH2:48][CH2:49][CH2:50][N:51]3[C:56](=[O:69])[CH2:57][CH2:58][CH2:59][O:60][C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([CH3:67])[C:62]=2[CH3:68])[CH:43]=[CH:44][CH:45]=1.[NH2:70][CH2:71][CH2:72][S:73]([OH:76])(=[O:75])=[O:74].N1(CCS(O)(=O)=O)CCNCC1>>[CH3:68][C:62]1[C:63]([CH3:67])=[CH:64][CH:65]=[CH:66][C:61]=1[O:60][CH2:59][CH2:58][CH2:57][C:56]([N:51]1[C:52]2[C:47](=[C:46]([C:42]3[CH:41]=[C:40]([CH:45]=[CH:44][CH:43]=3)[CH2:39][NH:38][C:21]([N:16]3[CH2:17][CH2:12][N:70]([CH2:71][CH2:72][S:73]([OH:76])(=[O:75])=[O:74])[CH2:14][CH2:15]3)=[O:34])[CH:55]=[CH:54][CH:53]=2)[CH2:48][CH2:49][CH2:50]1)=[O:69]

Participants

5

Reactant 4

HCID 1123TaurineHCID 4473182-piperazin-1-ylethanesulfonic AcidHCID 709819111-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-oneHCID 867125891-(5-(2-(3-Aminobenzyl)-2H-tetrazol-5-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

Product 1

HCID 867125902-(4-(3-(1-(4-(2,3-Dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamoyl)piperazin-1-yl)ethanesulfonic acid

Procedure

Example 118 was prepared using a procedure analogous to Example 115 except that 1-(5-(2-(3-aminobenzyl)-2H-tetrazol-5-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one was replaced with 1-(5-(3-(aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one and taurine was replaced with 2-(piperazin-1-yl)ethanesulfonic acid. LCMS, [M+H]+=649.3. 1H NMR (400 MHz, MeOD) δ 7.48-7.30 (m, 4H), 7.28-7.17 (m, 2H), 7.13-7.00 (m, 2H), 6.79 (d, J=7.5 Hz, 1H), 6.75 (d, J=8.2 Hz, 1H), 4.48 (s, 2H), 4.28 (br. s, 2H), 3.99 (t, J=5.2 Hz, 2H), 3.83 (t, J=7.0 Hz, 2H), 3.72 (br. s, 2H), 3.62 (t, J=6.9 Hz, 2H), 3.43-3.38 (m, 2H), 3.29 (t, J=6.9 Hz, 2H), 3.20 (br. s, 2H), 2.89 (t, J=7.0 Hz, 2H), 2.49 (t, J=6.1 Hz, 2H), 2.31-2.15 (m, 5H), 1.94 (s, 3H), 1.90-1.80 (m, 2H). HPLC-1: Rt=10.5 min, purity=99.3%; HPLC-2: Rt=10.4 min, purity=100%.

Workup

  1. customExample 118 was prepared

Sources & evidence

ORD record
ord-c85af0db7d0c4e1a9f5b327cd4a4e9b7
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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