(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879318Notes

Reaction equation

C(O[C@@H](C1C(C)=CC2N=C(N3C=CC=C(C4C=C5C(=CC=4)N(C)N=C5)C3=O)SC=2C=1C1C=CC(Cl)=CC=1)C(O)=O)(C)(C)C.[C:44]([O:48][C@@H:49]([C:54]1[C:79]([CH3:80])=[CH:78][C:57]2[N:58]=[C:59]([N:61]3[CH:66]=[C:65]([C:67]4[CH:68]=[C:69]5[C:73](=[CH:74][CH:75]=4)[N:72]([CH3:76])[N:71]=[CH:70]5)[CH:64]=[CH:63][C:62]3=[O:77])[S:60][C:56]=2[C:55]=1[C:81]1[CH:86]=[CH:85][C:84]([Cl:87])=[CH:83][CH:82]=1)[C:50]([O:52]C)=[O:51])([CH3:47])([CH3:46])[CH3:45]>>[C:44]([O:48][C@@H:49]([C:54]1[C:79]([CH3:80])=[CH:78][C:57]2[N:58]=[C:59]([N:61]3[CH:66]=[C:65]([C:67]4[CH:68]=[C:69]5[C:73](=[CH:74][CH:75]=4)[N:72]([CH3:76])[N:71]=[CH:70]5)[CH:64]=[CH:63][C:62]3=[O:77])[S:60][C:56]=2[C:55]=1[C:81]1[CH:82]=[CH:83][C:84]([Cl:87])=[CH:85][CH:86]=1)[C:50]([OH:52])=[O:51])([CH3:47])([CH3:45])[CH3:46]

Participants

Reactant 2

HCID 72194897(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid

HCID 86699836(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate

Product 1

HCID 72195018(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid

Procedure

Compound (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid was prepared following the procedure used to (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetic acid of Example 27, except that (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(5-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate was used instead of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)-2-oxopyridin-1(2H)-yl)benzo[d]thiazol-6-yl)acetate. 1H-NMR: 400 MHz, (CD3OD) δ 9.07 (d, J=2.8 Hz, 1H), 8.04 (s, 1H), 7.97 (s, 1H), 7.93 (dd, J=9.2, 2.4 Hz, 1H), 7.69-7.62 (m, 4H), 7.55-7.51 (m, 3H), 6.72 (d, J=9.6 Hz, 1H), 5.25 (s, 1H), 4.09 (s, 3H), 2.56 (s, 3H), 0.96 (s, 9H); LCMS-ESI+(m/z): [M+H]+ calcd for C33H30ClN4O4S: 613.17; Found: 613.2.

Sources & evidence

ORD record: ord-ef38462f8b8f46c18496aa2a060e8e86
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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