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

HRID 879321Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH3:32])[N:27]=[CH:26]5)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:36]1[CH:41]=[CH:40][C:39](Cl)=[CH:38][CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[C:43]([O:49]C[C@@H](OC(C)(C)C)C1C(C)=CC2N=C(C3C=CC=C(C4C=C5C(=CC=4)N(C)N=C5)C=3)SC=2C=1C1C=CC2OC(C)OC=2C=1)(=[O:48])[C:44](C)(C)C>>[C:1]([O:5][C@@H:6]([C:10]1[C:34]([CH3:35])=[CH:33][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH3:32])[N:27]=[CH:26]5)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:36]1[CH:41]=[CH:40][C:39]2[O:48][CH:43]([CH3:44])[O:49][C:38]=2[CH:37]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 72195435(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid

HCID 86699837(2S)-2-tert-butoxy-2-(5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)-7-(2-methylbenzo[d][1,3]dioxol-5-yl)benzo[d]thiazol-6-yl)ethyl pivalate

Product 1

HCID 72195436(2S)-2-tert-butoxy-2-(5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)-7-(2-methylbenzo[d][1,3]dioxol-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-(3-(1-methyl-1H-indazol-5-yl)phenyl)benzo[d]thiazol-6-yl)acetic acid in Method G, except using (2S)-2-tert-butoxy-2-(5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)-7-(2-methylbenzo[d][1,3]dioxol-5-yl)benzo[d]thiazol-6-yl)ethyl pivalate instead of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)phenyl)benzo[d]thiazol-6-yl)ethyl pivalate. LCMS-ESI+ (m/z): [M+H]+ calcd for C36H34N3O5S: 620.2; Found: 620.3; 1H-NMR: 400 MHz, (CD3OD) δ 8.34-8.32 (m, 1H), 8.08 (s, 2H), 8.00-7.94 (m, 1H), 7.85-7.84 (m, 3H), 7.66 (d, J=8.8 Hz, 1H), 7.59 (t, J=7.2 Hz, 1H), 7.17-7.11 (m, 1H), 7.06-7.00 (m, 1H), 6.97-6.94 (m, 1H), 6.43-6.37 (m, 1H), 5.46-5.36 (m, 1H), 4.10 (s, 3H), 2.60 (s, 3H), 1.74-1.68 (m, 3H), 0.99 (s, 9H).

Sources & evidence

ORD record: ord-4567dd8a0d9049369d251194a13ee23c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987250B2

Reaction notes

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