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

HRID 879496Notes

Reaction equation

C(O[C@@H](C1C(C)=CC2N=C(C3C=C4C(C(C5CCN(C)CC5)=NN4C)=CC=3)SC=2C=1C1C=CC(Cl)=CC=1)C(O)=O)(C)(C)C.[C:44]([O:48][C@@H:49]([C:55]1[C:80]([CH3:81])=[CH:79][C:58]2[N:59]=[C:60]([C:62]3[CH:63]=[C:64]4[C:68](=[CH:69][CH:70]=3)[N:67]([CH3:71])[N:66]=[C:65]4[C:72]3[CH2:73][CH2:74][N:75]([CH3:78])[CH2:76][CH:77]=3)[S:61][C:57]=2[C:56]=1[C:82]1[CH:87]=[CH:86][C:85]([Cl:88])=[CH:84][CH:83]=1)[C:50]([O:52]CC)=[O:51])([CH3:47])([CH3:46])[CH3:45]>>[C:44]([O:48][C@@H:49]([C:55]1[C:80]([CH3:81])=[CH:79][C:58]2[N:59]=[C:60]([C:62]3[CH:63]=[C:64]4[C:68](=[CH:69][CH:70]=3)[N:67]([CH3:71])[N:66]=[C:65]4[CH:72]3[CH2:77][CH2:76][N:75]([CH3:78])[CH2:74][CH2:73]3)[S:61][C:57]=2[C:56]=1[C:82]1[CH:83]=[CH:84][C:85]([Cl:88])=[CH:86][CH:87]=1)[C:50]([OH:52])=[O:51])([CH3:47])([CH3:45])[CH3:46]

Participants

Reactant 2

HCID 86700309(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-methylpiperidin-4-yl)-1H-indazol-6-yl)benzo[d]thiazol-6-yl)acetic acid

HCID 86700312(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700313(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-methylpiperidin-4-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetic acid

Procedure

Prepared in a similar manner as (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-methylpiperidin-4-yl)-1H-indazol-6-yl)benzo[d]thiazol-6-yl)acetic acid except using (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indazol-5-yl)benzo[d]thiazol-6-yl)acetate instead of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-methyl-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indazol-6-yl)benzo[d]thiazol-6-yl)acetate. LCMS-ESI+: calc'd for C34H37ClN4O3S: 617.2, 619.2 (M+H+); Found: 617.3, 619.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 8.47 (s, 1H), 8.13 (dd, J=8.9, 1.5 Hz, 1H), 7.83 (s, 1H), 7.74-7.54 (m, 5H), 5.26 (s, 1H), 4.10 (s, 0.3H, minor diastereomer), 4.06 (s, 2.7H, major diastereomer), 3.76-3.60 (m, 2H), 3.58-3.39 (m, 2H), 3.30-3.19 (m, 2H), 2.97 (s, 2.7H, major diastereomer), 2.94 (s, 0.3H, minor diastereomer), 2.63 (s, 3H), 2.49-2.29 (m, 2H), 2.29-2.09 (m, 1H), 0.99 (s, 9H).

Sources & evidence

ORD record: ord-8aa57c4ef8024b09899e23ffe1ec9d56
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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