2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(4-(hydroxymethyl)phenyl)thiazole-4-carboxylic acid → HCID 178509382, compound

HRID 1518319Notes

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:53]=[C:54]([CH:96]=[CH:97][CH:98]=2)[O:55][CH2:56][C:57]2[S:61][C:60]([N:62]3[CH2:71][CH2:70][C:69]4[C:64](=[C:65]([C:72](=[O:91])/[N:73]=[C:74]5/[S:75][C:76]6[CH:90]=[CH:89][CH:88]=[CH:87][C:77]=6[N:78]/5COCC[Si](C)(C)C)[CH:66]=[CH:67][CH:68]=4)[CH2:63]3)=[N:59][C:58]=2[C:92]([O:94]C)=[O:93])[C:41]=1[C:99]#[N:100]>>[NH2:39][C:40]1[NH:44][N:43]=[C:42]([C:52]2[CH:53]=[C:54]([CH:96]=[CH:97][CH:98]=2)[O:55][CH2:56][C:57]2[S:61][C:60]([N:62]3[CH2:71][CH2:70][C:69]4[C:64](=[C:65]([C:72](=[O:91])[NH:73][C:74]5[S:75][C:76]6[CH:90]=[CH:89][CH:88]=[CH:87][C:77]=6[N:78]=5)[CH:66]=[CH:67][CH:68]=4)[CH2:63]3)=[N:59][C:58]=2[C:92]([OH:94])=[O:93])[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 178499110HCID 178499110, compound

Product 1

HCID 178509382HCID 178509382, compound

Procedure

The title compound 46 was prepared in a similar manner to the synthesis of compound 34 by substituting compound 34D with compound 46A in step 5 of Example 34: 1H NMR (DMSO-d6): δ 12.83 (s, 1H), 7.96 (d, J=7.93 Hz, 1H), 7.72 (d, J=7.93 Hz, 1H), 7.61 (d, J=7.32 Hz, 1H), 7.27-7.42 (m, 7H), 6.95 (d, J=7.93 Hz, 1H), 5.47 (s, 2H), 4.72-4.81 (m, 4H), 3.74 (t, J=5.68 Hz, 2H), 2.98 (t, J=5.65 Hz, 2H). MS (ESI(+)): m/z 649 (M+H).

Sources & evidence

ORD record: ord-b3627d6cd8b54be6b492717654b0b4b4
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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