tert-butyl 5-amino-4-cyano-3-(3-hydroxyphenyl)-1H-pyrazole-1-carboxylate → ethyl 5-(4-((3-(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

HRID 1518299Notes

Reaction equation

HRID 1518299 reaction equation
NC1N(C(OC(C)(C)C)=O)N=C(C2C=CC(O[CH2:19][C:20]3[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)[CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[CH:35]=[CH:36][CH:37]=6)[CH2:32]5)=[N:28][C:27]=4[C:61]([O:63][CH2:64][CH3:65])=[O:62])=[CH:22][CH:21]=3)=CC=2)C=1C#N.[NH2:70][C:71]1[N:75]([C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])[N:74]=[C:73]([C:83]2[CH:88]=[CH:87][CH:86]=[C:85]([OH:89])[CH:84]=2)[C:72]=1[C:90]#[N:91]>>[NH2:70][C:71]1[N:75]([C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])[N:74]=[C:73]([C:83]2[CH:84]=[C:85]([CH:86]=[CH:87][CH:88]=2)[O:89][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[S:30][C:29]([N:31]4[CH2:40][CH2:39][C:38]5[C:33](=[C:34]([C:41](=[O:60])[N:42]([C:51]6[S:52][C:53]7[CH:59]=[CH:58][CH:57]=[CH:56][C:54]=7[N:55]=6)[CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:48])([CH3:49])[CH3:50])[CH:35]=[CH:36][CH:37]=5)[CH2:32]4)=[N:28][C:27]=3[C:61]([O:63][CH2:64][CH3:65])=[O:62])=[CH:24][CH:25]=2)[C:72]=1[C:90]#[N:91]

Participants

3

Reactant 2

HCID 59447530tert-butyl 5-amino-4-cyano-3-(3-hydroxyphenyl)-1H-pyrazole-1-carboxylateHCID 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-carboxylate

Product 1

HCID 86761596ethyl 5-(4-((3-(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

Procedure

The title compound 37A was prepared in a similar manner to the synthesis of compound 35A by substituting compound 31F with compound 36A as a mixture of two inseparable isomers: MS (ESI(+)): m/z 984 (M+H).

Workup

  1. additionas a mixture of two inseparable isomers

Sources & evidence

ORD record
ord-3f04ad67aec94596a02710f657508966
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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