Acetic Acid → HCID 86700328, compound

HRID 879507Notes

Reaction equation

HRID 879507 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:43]([CH3:44])=[CH:42][C:15]2[N:16]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:21]([C:32]4[CH:33]=[C:34]5[C:38](=[CH:39][CH:40]=4)[N:37]([CH3:41])[N:36]=[CH:35]5)[CH2:20]3)[S:18][C:14]=2[C:13]=1[C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:43]([CH3:44])=[CH:42][C:15]2[N:16]=[C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH:21]([C:32]4[CH:33]=[C:34]5[C:38](=[CH:39][CH:40]=4)[N:37]([CH3:41])[N:36]=[CH:35]5)[CH2:20]3)[S:18][C:14]=2[C:13]=1[C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86700327HCID 86700327, compound

Product 1

HCID 86700328HCID 86700328, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To the solution of tert-butyl 4-(6-((S)-1-tert-butoxy-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-2-(1-methyl-1H-indazol-5-yl)piperazine-1-carboxylate (5 mg) in THF/MeOH (0.5 mL/0.5 mL) was added sodium hydroxide solution (0.4 mL, 1.0 N). The mixture was heated at 50° C. for 16 hours. The mixture was cooled, and was acidified with acetic acid (60 μL). Concentration and purification with reverse phase HPLC gave (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. LCMS-ESI+: calc'd for C37H43ClN5O5S: 704.3 (M+H+); Found: 704.1 (M+H+). 1H-NMR 400 MHz, (CD3OD) δ 7.96 (s, 1H), 7.64 (m, 2H), 7.49 (m, 3H), 7.38 (m, 3H), 5.46 (m, 1H), 5.19 (s, 1H), 4.4 (m, 1H), 4.2 (m, 1H), 4.07 (s, 3H), 4.0-3.7 (m, 2H), 3.5 (m, 2H), 2.5 (s, 3H), 1.40 (s, 9H), 0.98 (s, 9H).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationConcentration and purification with reverse phase HPLC

Sources & evidence

ORD record
ord-7f080e36ab6c47458ed71c662643be9b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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