4-(4-Hydroxyphenyl)thiophene-3-carbonitrile → HCID 178499106, compound

HRID 1518343Notes

Reaction equation

HRID 1518343 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.O[CH2:93][C:94]1[S:98][C:97]([N:99]2[CH2:108][CH2:107][C:106]3[C:101](=[C:102]([C:109](=[O:128])/[N:110]=[C:111]4/[S:112][C:113]5[CH:127]=[CH:126][CH:125]=[CH:124][C:114]=5[N:115]/4[CH2:116][O:117][CH2:118][CH2:119][Si:120]([CH3:123])([CH3:122])[CH3:121])[CH:103]=[CH:104][CH:105]=3)[CH2:100]2)=[N:96][C:95]=1[C:129]([O:131][CH3:132])=[O:130].[OH:133][C:134]1[CH:139]=[CH:138][C:137]([C:140]2[C:141]([C:145]#[N:146])=[CH:142][S:143][CH:144]=2)=[CH:136][CH:135]=1>>[C:145]([C:141]1[C:140]([C:137]2[CH:136]=[CH:135][C:134]([OH:133])=[C:139]([CH:138]=2)[CH2:93][C:94]2[S:98][C:97]([N:99]3[CH2:108][CH2:107][C:106]4[C:101](=[C:102]([C:109](=[O:128])/[N:110]=[C:111]5/[S:112][C:113]6[CH:127]=[CH:126][CH:125]=[CH:124][C:114]=6[N:115]/5[CH2:116][O:117][CH2:118][CH2:119][Si:120]([CH3:121])([CH3:123])[CH3:122])[CH:103]=[CH:104][CH:105]=4)[CH2:100]3)=[N:96][C:95]=2[C:129]([O:131][CH3:132])=[O:130])=[CH:144][S:143][CH:142]=1)#[N:146]

Participants

5

Reactant 4

HCID 594475724-(4-Hydroxyphenyl)thiophene-3-carbonitrileHCID 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-carboxylateHCID 178499108HCID 178499108, compound

Product 1

HCID 178499106HCID 178499106, compound

Procedure

The title compound 60A was prepared in a similar manner to the synthesis of compound 35A by substituting compound 34D and compound 31F with compound 45D and compound 51A, respectively: ESI (+)/LC/MS: 892 (M+NH4—H2O)+: 1H NMR (DMSO-d6): δ 9.99 (s, 1H), 8.58 (s, 1H), 8.21 (d, J=6.71 Hz, 1H), 7.92 (d, J=7.32 Hz, 1H), 7.66-7.68 (m, 2H), 7.52-7.55 (m, 1H), 7.32-7.41 (m, 5H), 6.92 (d, J=8.24 Hz, 1H), 5.97 (s, 2H), 5.08 (s, 2H), 4.35 (s, 2H), 3.78 (s, 3H), 3.64-3.68 (m, 2H), 2.98 (t, J=5.8 Hz, 2H), 0.84-0.87 (m, 2H), −0.22 (s, 9H). ESI (+)/MS: 794 (M+H)+.

Sources & evidence

ORD record
ord-6bc5a4f7d5ef401887993b2e30ef44c3
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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