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 → HCID 178499109, compound

HRID 1518316Notes

Reaction equation

[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([C:14]2[CH:67]=[CH:66][C:17](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)=[CH:16][CH:15]=2)[C:3]=1[C:68]#[N:69].[OH:70][CH2:71][C:72]1[S:76][C:75]([N:77]2[CH2:86][CH2:85][C:84]3[C:79](=[C:80]([C:87](=[O:106])/[N:88]=[C:89]4/[S:90][C:91]5[CH:105]=[CH:104][CH:103]=[CH:102][C:92]=5[N:93]/4[CH2:94][O:95][CH2:96][CH2:97][Si:98]([CH3:101])([CH3:100])[CH3:99])[CH:81]=[CH:82][CH:83]=3)[CH2:78]2)=[N:74][C:73]=1[C:107]([O:109][CH3:110])=[O:108]>>[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([C:14]2[CH:67]=[CH:66][C:17]([O:70][CH2:71][C:72]3[S:76][C:75]([N:77]4[CH2:86][CH2:85][C:84]5[C:79](=[C:80]([C:87](=[O:106])/[N:88]=[C:89]6/[S:90][C:91]7[CH:105]=[CH:104][CH:103]=[CH:102][C:92]=7[N:93]/6[CH2:94][O:95][CH2:96][CH2:97][Si:98]([CH3:101])([CH3:100])[CH3:99])[CH:81]=[CH:82][CH:83]=5)[CH2:78]4)=[N:74][C:73]=3[C:107]([O:109][CH3:110])=[O:108])=[CH:16][CH:15]=2)[C:3]=1[C:68]#[N:69]

Participants

Reactant 2

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-carboxylate

HCID 178499108HCID 178499108, compound

Product 1

HCID 178499109HCID 178499109, compound

Procedure

Compound 45E was prepared in a similar manner to the synthesis of compound 35A by substituting compound 34D with compound 45D in step 1 of Example 35: 1H NMR (DMSO-d6): δ 8.24 (dd, J=7.52, 1.38 Hz, 1H), 7.94 (d, J=7.67 Hz, 1H), 7.70 (d, J=7.98 Hz, 1H), 7.67 (s, 2H), 7.53-7.57 (m, 1H), 7.34-7.43 (m, 3H), 7.10-7.14 (m, 2H), 6.00 (s, 2H), 5.57 (s, 2H), 5.17 (s, 2H), 3.81 (s, 3H), 3.76 (t, J=5.98 Hz, 2H), 3.66-3.70 (m, 2H), 3.04 (t, J=6.14 Hz, 2H), 0.85-0.89 (m, 2H), −0.20 (s, 9H). MS (ESI(+)): m/z 892 (M+NH4—H2O).

Sources & evidence

ORD record: ord-1fb521d7dad14556832832acbf82fe60
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

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