Hydrochloric Acid → HCID 59900482, compound

HRID 2228787Notes

Reaction equation

HRID 2228787 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH:37]C(=O)OC(C)(C)C)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][NH:13][C:14]2[C:19](=[O:20])[N:18]([CH2:21][C:22]([NH:24][CH2:25][C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[NH:31][CH:30]=[C:29]4[CH3:35])=[O:23])[C:17]([CH3:36])=[CH:16][N:15]=2)[CH:6]=1.Cl.[OH-].[Na+]>CO>[NH2:37][CH:4]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][CH2:12][NH:13][C:14]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([NH:24][CH2:25][C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[C:29]3[CH3:35])=[O:23])[C:17]([CH3:36])=[CH:16][N:15]=1)[CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59900604HCID 59900604, compound

Product 1

HCID 59900482HCID 59900482, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl (1R/S)-2-methoxy-1-[3-(2-{[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}ethyl)phenyl]ethylcarbamate (preparation 124) (26 mg, 0.043 mmol) in hydrochloric acid (2 ml, 6N, 12 mmol) and methanol (2 ml), was stirred under a nitrogen atmosphere for 3 hrs. The reaction mixture was basified to pH 10 using 1N NaOH solution, extracted with dichloromethane (4×10 ml), and ethyl acetate (3×10 ml). The combined organic extracts were dried over MgSO4, and evaporated under reduced pressure to give the title compound as a white solid, (13 mg, 60%). Both R, and S isomers are present although their relative proportions have not been determined.

Workup

  1. extractionextracted with dichloromethane (4×10 ml), and ethyl acetate (3×10 ml)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba80c7de1424444aa986d5d704d7be7c
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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