Hydrochloric Acid → HCID 86700329, compound

HRID 879508Notes

Reaction equation

HRID 879508 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:41]([CH3:42])=[CH:40][C:13]2[N:14]=[C:15]([N:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH:19]([C:30]4[CH:31]=[C:32]5[C:36](=[CH:37][CH:38]=4)[N:35]([CH3:39])[N:34]=[CH:33]5)[CH2:18]3)[S:16][C:12]=2[C:11]=1[C:43]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].Cl.CC(O)C>>[C:1]([O:5][C@@H:6]([C:10]1[C:41]([CH3:42])=[CH:40][C:13]2[N:14]=[C:15]([N:17]3[CH2:22][CH2:21][NH:20][CH:19]([C:30]4[CH:31]=[C:32]5[C:36](=[CH:37][CH:38]=4)[N:35]([CH3:39])[N:34]=[CH:33]5)[CH2:18]3)[S:16][C:12]=2[C:11]=1[C:43]1[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 86700328HCID 86700328, compound

Product 1

HCID 86700329HCID 86700329, compound

Procedure

To (2S)-2-tert-butoxy-2-(2-(4-(tert-butoxycarbonyl)-3-(1-methyl-1H-indazol-5-yl)piperazin-1-yl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid (4 mg) was added hydrochloric acid in 2-propanol (3 mL, 0.5 N, 1.5 mmol). The mixture was stirred for 24 hours. Concentration and purification with reverse phase HPLC gave (2S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(1-methyl-1H-indazol-5-yl)piperazin-1-yl)benzo[d]thiazol-6-yl)acetic acid. LCMS-ESI+: calc'd for C32H35ClN5O3S: 604.2 (M+H+); Found: 604.3 (M+H+). 1H-NMR 400 MHz, (CD3OD) δ 8.10 (s, 1H), 7.97 (s, 1H), 7.72 (m, 1H), 7.6-7.4 (m, 5H), 7.38 (s, 1H), 5.15 (s, 1H), 4.7 (m, 1H), 4.45 (m, 1H), 4.26 (m, 1H), 4.11 (s, 3H), 3.8 (m, 1H), 3.65-3.4 (m, 3H), 2.50 (s, 3H), 0.94 (s, 9H);

Workup

  1. concentrationConcentration and purification with reverse phase HPLC

Sources & evidence

ORD record
ord-0411a45e524d4472a67a985dc3f2a658
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…