2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-cyano-thiophen-3-yl)-phenoxy]-propyl]-thiazole-4-carboxylic acid → HCID 59447566, compound

HRID 1518352Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10]C(C1C=CC=C2C=1CN(C1SC(CCCOC3C=CC(C4C(C#N)=CSC=4)=CC=3)=C(C(O)=O)N=1)CC2)=O.[N+:48]([C:51]1[CH:52]=[C:53]([S:57]([NH:60][CH2:61][CH2:62][C:63]2[S:67][C:66]([N:68]3[CH2:77][CH2:76][C:75]4[C:70](=[C:71]([C:78](=[O:97])/C=C5/SC6C=CC=CC=6N/5COCC[Si](C)(C)C)[CH:72]=[CH:73][CH:74]=4)[CH2:69]3)=[N:65][C:64]=2[C:98]([O:100]CC)=[O:99])(=[O:59])=[O:58])[CH:54]=[CH:55][CH:56]=1)([O-:50])=[O:49]>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:78]([C:71]1[CH:72]=[CH:73][CH:74]=[C:75]2[C:70]=1[CH2:69][N:68]([C:66]1[S:67][C:63]([CH2:62][CH2:61][NH:60][S:57]([C:53]3[CH:54]=[CH:55][CH:56]=[C:51]([N+:48]([O-:50])=[O:49])[CH:52]=3)(=[O:59])=[O:58])=[C:64]([C:98]([OH:100])=[O:99])[N:65]=1)[CH2:77][CH2:76]2)=[O:97]

Participants

Reactant 2

HCID 468362452-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-cyano-thiophen-3-yl)-phenoxy]-propyl]-thiazole-4-carboxylic acid

HCID 59447549HCID 59447549, compound

Product 1

HCID 59447566HCID 59447566, compound

Procedure

The title compound 70 was prepared in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 70A: 1H NMR (DMSO-d6): δ 8.39-8.44 (m, 2H), 8.11-8.15 (m, 2H), 8.04 (d, J=7.98 Hz, 1H), 7.78-7.84 (m, 2H), 7.68 (d, J=7.36 Hz, 1H), 7.34-7.50 (m, 4H), 6.90 (d, J=8.29 Hz, 1H), 4.79 (s, 2H), 3.69 (d, J=5.98 Hz, 2H), 3.06-3.10 (m, 4H), 3.03 (t, J=5.98 Hz, 2H). ESI (+)/MS: 665 (M+H)+.

Sources & evidence

ORD record: ord-854f83b7e5c243479cb092d192658b4c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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