Hydrochloric Acid → Bcl-xL antagonist 2

HRID 333872Notes

Reaction equation

HRID 333872 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][CH:25]=[C:26]([C:28]([O:30]C)=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[OH-].[Na+].Cl>O1CCCC1.CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59447460methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

Product 1

HCID 46836567Bcl-xL antagonist 2

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 1C (180 mg) in tetrahydrofuran (4 mL) and methanol (2 mL) was added 2N NaOH (2 mL). The mixture was stirred at 50° C. for 4 hours, cooled and neutralized by the slow addition of 5% aqueous HCl. The precipitates were collected by filtration and dried to provide the title compound.

Workup

  1. temperaturecooled
  2. filtrationThe precipitates were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-adcaaf8595034e6a8fa767549edc5f47
Source dataset
uspto-grants-2014_11
Patent number
US08883784B2

Reaction notes

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