Ethyl 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate → 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetic acid

HRID 2381685Notes

Reaction equation

HRID 2381685 reaction equation
[CH:1]1([NH:5][C:6]2[C:7]3[CH:32]=[CH:31][NH:30][C:8]=3[N:9]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][C:24]([O:26]CC)=[O:25])[C:18](=[O:29])[CH2:17][CH2:16]4)[N:11]=2)[CH2:4][CH2:3][CH2:2]1>C1COCC1.O.[OH-].[Na+]>[CH:1]1([NH:5][C:6]2[C:7]3[CH:32]=[CH:31][NH:30][C:8]=3[N:9]=[C:10]([NH:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][C:24]([OH:26])=[O:25])[C:18](=[O:29])[CH2:17][CH2:16]4)[N:11]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 1

HCID 57990398Ethyl 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate

Product 1

HCID 579903132-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetate (10 mg, 0.023 mmol) in THF (0.6 mL) and H2O (0.4 mL) was added NaOH (5N, 2 drops). After stirring for 3 h at room temperature, the reaction mixture was purified by preparative HPLC to yield 2-(6-(4-(cyclobutyamino)-7H-pyrrolo[2,3-d]pyrimidine-2-ylamino)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetic acid (MS calcd for C21H22N6O3 406.2, found [MH] 407.0; UV 207.5, 304.5 nm).

Workup

  1. customthe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-ae4f709087e241baa9d9d494ef0a41cf
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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