ethyl 5-(4-((4-(5-amino-1-(tert-butoxycarbonyl)-4-cyano-1H-pyrazol-3-yl)phenoxy)methyl)phenyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate → tert-butyl 6-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4-(5-(2-(dimethylamino)ethoxy)pyridin-2-yl)phenoxy)propyl)picolinate

HRID 1518391Notes

Reaction equation

HRID 1518391 reaction equation
NC1N(C(OC(C)(C)C)=O)N=C(C2C=CC(OCC3C=CC(C4SC(N5CCC6C(=C([C:41](=[O:60])[N:42]([C:51]7[S:52][C:53]8[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=8[N:55]=7)[CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])C=CC=6)C5)=NC=4C(OCC)=O)=CC=3)=CC=2)C=1C#N.NC1N(C(OC(C)(C)C)=O)N=C(C2C=CC(O)=CC=2)C=1C#N.[OH:92][CH2:93][CH2:94][CH2:95][C:96]1[C:97]([C:132]([O:134][C:135]([CH3:138])([CH3:137])[CH3:136])=[O:133])=[N:98][C:99]([N:102]2[CH2:111][CH2:110][C:109]3[C:104](=[C:105](C(=O)/N=C4\SC5C=CC=CC=5N\4COCC[Si](C)(C)C)[CH:106]=[CH:107][CH:108]=3)[CH2:103]2)=[CH:100][CH:101]=1.[CH3:139][N:140]([CH3:157])[CH2:141][CH2:142][O:143][C:144]1[CH:145]=[CH:146][C:147]([C:150]2[CH:155]=[CH:154][C:153](O)=[CH:152][CH:151]=2)=[N:148][CH:149]=1>>[S:52]1[C:53]2[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=2[N:55]=[C:51]1[N:42]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:48])[CH3:49])[C:41]([C:105]1[CH:106]=[CH:107][CH:108]=[C:109]2[C:104]=1[CH2:103][N:102]([C:99]1[N:98]=[C:97]([C:132]([O:134][C:135]([CH3:138])([CH3:137])[CH3:136])=[O:133])[C:96]([CH2:95][CH2:94][CH2:93][O:92][C:153]3[CH:152]=[CH:151][C:150]([C:147]4[CH:146]=[CH:145][C:144]([O:143][CH2:142][CH2:141][N:140]([CH3:157])[CH3:139])=[CH:149][N:148]=4)=[CH:155][CH:154]=3)=[CH:101][CH:100]=1)[CH2:111][CH2:110]2)=[O:60]

Participants

5

Reactant 4

HCID 59447596ethyl 5-(4-((4-(5-amino-1-(tert-butoxycarbonyl)-4-cyano-1H-pyrazol-3-yl)phenoxy)methyl)phenyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylateHCID 1360277234-(5-(2-(Dimethylamino)ethoxy)pyridin-2-yl)phenolHCID 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylateHCID 178450838HCID 178450838, compound

Product 1

HCID 59447458tert-butyl 6-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(4-(5-(2-(dimethylamino)ethoxy)pyridin-2-yl)phenoxy)propyl)picolinate

Procedure

Compound 95A was prepared in a similar manner to the synthesis of compound 35A by substituting compound 34D and compound 31F with compound 94F and compound 90B, respectively: ESI (+)LC/MS: 915 (M+H2O—NH4)+.

Sources & evidence

ORD record
ord-437c1ffa99f94719a88e0097ff52951e
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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