2-(Dimethylamino)ethanol → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-(3-{4-[5-(2-dimethylamino-ethoxy)-pyridin-2-yl]-phenoxy}-propyl)-thiazole-4-carboxylic acid

HRID 1518379Notes

Reaction equation

HRID 1518379 reaction equation
NC1N(C(OC(C)(C)C)=O)N=C(C2C=CC(OCC3[CH:25]=[CH:24][C:23]([C:26]4[S:30][C:29]([N:31]5[CH2:40][CH2:39][C:38]6[C:33](=[C:34]([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)COCC[Si](C)(C)C)[CH:35]=[CH:36][CH:37]=6)[CH2:32]5)=[N:28][C:27]=4[C:61]([O:63]CC)=[O:62])=CC=3)=CC=2)C=1C#N.NC1N(C(OC(C)(C)C)=O)[N:74]=[C:73]([C:83]2[CH:88]=[CH:87][C:86]([OH:89])=[CH:85][CH:84]=2)[C:72]=1[C:90]#N.[CH3:92][N:93]([CH3:97])[CH2:94][CH2:95][OH:96].Cl[C:99]1N=CC(O)=C[CH:100]=1>>[S:52]1[C:53]2[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=2[N:55]=[C:51]1[NH:42][C:41]([C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:33]=1[CH2:32][N:31]([C:29]1[S:30][C:26]([CH2:23][CH2:24][CH2:25][O:89][C:86]3[CH:85]=[CH:84][C:83]([C:73]4[CH:72]=[CH:90][C:100]([O:96][CH2:95][CH2:94][N:93]([CH3:97])[CH3:92])=[CH:99][N:74]=4)=[CH:88][CH:87]=3)=[C:27]([C:61]([OH:63])=[O:62])[N:28]=1)[CH2:40][CH2:39]2)=[O:60]

Participants

5

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 8198212-Chloro-5-hydroxypyridineHCID 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 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 468368002-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-(3-{4-[5-(2-dimethylamino-ethoxy)-pyridin-2-yl]-phenoxy}-propyl)-thiazole-4-carboxylic acid

Procedure

Compound 90 was prepared in a similar manner to the synthesis of compound 35A by substituting compound 34C and compound 31F with 2-(dimethylamino)ethanol and 6-chloropyridin-3-ol, respectively.

Sources & evidence

ORD record
ord-85577796d0ff43ffb4aa990460495044
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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