Acetic Acid → 2-(1-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetic acid

HRID 2281527Notes

Reaction equation

HRID 2281527 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:12][C:13]3[N:14]=[C:15]([N:22]4[CH2:27][CH2:26][CH:25]([CH2:28][C:29]([O:31]CCCC)=[O:30])[CH2:24][CH2:23]4)[C:16]4[CH:21]=[CH:20][NH:19][C:17]=4[N:18]=3)[CH:8]=2)[NH:3]1.[Li+].[OH-].CC(O)=O>C1COCC1>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:12][C:13]3[N:14]=[C:15]([N:22]4[CH2:23][CH2:24][CH:25]([CH2:28][C:29]([OH:31])=[O:30])[CH2:26][CH2:27]4)[C:16]4[CH:21]=[CH:20][NH:19][C:17]=4[N:18]=3)[CH:8]=2)[NH:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium Hydroxide2×HCID 57990317butyl 2-(1-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetate

Product 1

HCID 579903442-(1-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetic acidYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of butyl 2-(1-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)acetate (48 mg, 0.101 mmol) in THF (2 mL), aq. 1N LiOH (1.00 mL, 1.00 mmol) was added. The mixture was stirred at room temperature for 20 h. HOAc (1 mL) was added to neutralize LiOH. It was then purified by HPLC to give the titled compound (32 mg). MS 421.3 (M+H); UV 207.8, 279.8 nm

Workup

  1. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-9b0017e4bbea4ab18a96d31b40609c3f
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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