2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylic acid → HCID 178509392, compound

HRID 1518307Notes

Reaction equation

S1C2C=CC=CC=2N=C1NC(C1C=CC=C2C=1CN(C1SC(C3C=CC(CO)=CC=3)=C(C(O)=O)N=1)CC2)=O.[NH2:39][C:40]1[N:44](C(OC(C)(C)C)=O)[N:43]=[C:42]([C:52]2[CH:100]=[CH:99][C:55]([O:56][CH2:57][C:58]#[C:59][C:60]3[S:64][C:63]([N:65]4[CH2:74][CH2:73][C:72]5[C:67](=[C:68]([C:75](=[O:93])[N:76]([C:84]6[S:85][C:86]7[CH:92]=[CH:91][CH:90]=[CH:89][C:87]=7[N:88]=6)C(OC(C)(C)C)=O)[CH:69]=[CH:70][CH:71]=5)[CH2:66]4)=[N:62][C:61]=3[C:94]([O:96]CC)=[O:95])=[CH:54][CH:53]=2)[C:41]=1[C:101]#[N:102]>>[NH2:39][C:40]1[NH:44][N:43]=[C:42]([C:52]2[CH:53]=[CH:54][C:55]([O:56][CH2:57][C:58]#[C:59][C:60]3[S:64][C:63]([N:65]4[CH2:74][CH2:73][C:72]5[C:67](=[C:68]([C:75](=[O:93])[NH:76][C:84]6[S:85][C:86]7[CH:92]=[CH:91][CH:90]=[CH:89][C:87]=7[N:88]=6)[CH:69]=[CH:70][CH:71]=5)[CH2:66]4)=[N:62][C:61]=3[C:94]([OH:96])=[O:95])=[CH:99][CH:100]=2)[C:41]=1[C:101]#[N:102]

Participants

Reactant 2

HCID 468370542-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylic acid

HCID 86644323ethyl 5-(3-(4-(5-amino-1-(tert-butoxycarbonyl)-4-cyano-1H-pyrazol-3-yl)phenoxy)prop-1-ynyl)-2-(8-(benzo[d]thiazol-2-yl(tert-butoxycarbonyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

Product 1

HCID 178509392HCID 178509392, compound

Procedure

The title compound 40 was prepared in a similar manner to the synthesis of compound 34 by substituting compound 34D with compound 40A: 1H NMR (DMSO-d6): δ 8.03 (d, J=7.98 Hz, 1H), 7.60-7.80 (m, 5H), 7.34-7.50 (m, 6H), 7.32-7.49 (m, 6H), 7.12 (d, J=8.9 Hz, 2H), 5.10 (s, 2H), 4.91 (s, 2H), 3.73-3.75 (m, 2H), 3.05-3.07 (m, 2H). MS (ESI(+)): m/z 673 (M+H).

Sources & evidence

ORD record: ord-f506c34fb8234bfcad3fa958619bf1a9
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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