2-Amino-4-(4-hydroxyphenyl)thiophene-3-carbonitrile → methyl 5-(3-(4-(5-amino-4-cyanothiophen-3-yl)phenoxy)propyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

HRID 1518325Notes

Reaction equation

HRID 1518325 reaction equation
NC1N(C(OC(C)(C)C)=O)N=C(C2C=CC(OCC3C=CC(C4SC(N5CCC6C(=C(C(=O)N(C7SC8C=CC=CC=8N=7)COCC[Si](C)(C)C)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.[S:92]1[C:96]2[CH:97]=[CH:98][CH:99]=[CH:100][C:95]=2[N:94]=[C:93]1[N:101]([CH2:127][O:128][CH2:129][CH2:130][Si:131]([CH3:134])([CH3:133])[CH3:132])[C:102]([C:104]1[CH:105]=[CH:106][CH:107]=[C:108]2[C:113]=1[CH2:112][N:111]([C:114]1[S:115][C:116]([CH2:123][CH2:124][CH2:125][OH:126])=[C:117]([C:119]([O:121][CH3:122])=[O:120])[N:118]=1)[CH2:110][CH2:109]2)=[O:103].[NH2:135][C:136]1[S:137][CH:138]=[C:139]([C:143]2[CH:148]=[CH:147][C:146](O)=[CH:145][CH:144]=2)[C:140]=1[C:141]#[N:142]>>[NH2:135][C:136]1[S:137][CH:138]=[C:139]([C:143]2[CH:148]=[CH:147][C:146]([O:126][CH2:125][CH2:124][CH2:123][C:116]3[S:115][C:114]([N:111]4[CH2:110][CH2:109][C:108]5[C:113](=[C:104]([C:102](=[O:103])[N:101]([C:93]6[S:92][C:96]7[CH:97]=[CH:98][CH:99]=[CH:100][C:95]=7[N:94]=6)[CH2:127][O:128][CH2:129][CH2:130][Si:131]([CH3:134])([CH3:133])[CH3:132])[CH:105]=[CH:106][CH:107]=5)[CH2:112]4)=[N:118][C:117]=3[C:119]([O:121][CH3:122])=[O:120])=[CH:145][CH:144]=2)[C:140]=1[C:141]#[N:142]

Participants

5

Reactant 4

HCID 152199602-Amino-4-(4-hydroxyphenyl)thiophene-3-carbonitrileHCID 59447477methyl 2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-hydroxypropyl)thiazole-4-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-carboxylateHCID 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylate

Product 1

HCID 59447498methyl 5-(3-(4-(5-amino-4-cyanothiophen-3-yl)phenoxy)propyl)-2-(8-(benzo[d]thiazol-2-yl((2-(trimethylsilyl)ethoxy)methyl)carbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

Procedure

Compound 47G was prepared in a similar manner to the synthesis of compound 35A by substituting compound 34B and compound 31F with compound 47F and compound 47C, respectively: MS (ESI(+)): m/z 838 (M+H).

Sources & evidence

ORD record
ord-9540a2846e104d689f8e4feaf0b993fe
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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