2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylic acid → HCID 178509391, compound

HRID 1518317Notes

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:98]=[CH:97][C:55]([O:56][CH2:57][C:58]3[S:62][C:61]([N:63]4[CH2:72][CH2:71][C:70]5[C:65](=[C:66]([C:73](=[O:92])/[N:74]=[C:75]6/[S:76][C:77]7[CH:91]=[CH:90][CH:89]=[CH:88][C:78]=7[N:79]/6COCC[Si](C)(C)C)[CH:67]=[CH:68][CH:69]=5)[CH2:64]4)=[N:60][C:59]=3[C:93]([O:95]C)=[O:94])=[CH:54][CH:53]=2)[C:41]=1[C:99]#[N:100]>>[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]3[S:62][C:61]([N:63]4[CH2:72][CH2:71][C:70]5[C:65](=[C:66]([C:73](=[O:92])[NH:74][C:75]6[S:76][C:77]7[CH:91]=[CH:90][CH:89]=[CH:88][C:78]=7[N:79]=6)[CH:67]=[CH:68][CH:69]=5)[CH2:64]4)=[N:60][C:59]=3[C:93]([OH:95])=[O:94])=[CH:97][CH:98]=2)[C:41]=1[C:99]#[N:100]

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 178499109HCID 178499109, compound

Product 1

HCID 178509391HCID 178509391, compound

Procedure

The title compound 45 was prepared in a similar manner to the synthesis of compound 34 by substituting compound 34D with compound 45E: 1H NMR (DMSO-d6): δ 8.02 (d, J=7.67 Hz, 1H), 7.78 (d, J=7.98 Hz, 1H), 7.59-7.71 (m, 3H), 7.33-7.48 (m, 4H), 7.05 (d, J=7.59 Hz, 1H), 6.83 (d, J=7.67 Hz, 1H), 5.54 (s, 2H), 4.77-4.86 (m, 4H), 3.74 (t, J=5.68 Hz, 2H), 3.04 (t, J=5.83 Hz, 2H). MS (ESI(+)): m/z 647 (M−H).

Sources & evidence

ORD record: ord-2435dc9b47aa45cbaa001c8f78dea3b5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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