Acetic Acid → HCID 178473883, compound

HRID 2281523Notes

Reaction equation

HRID 2281523 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:25]=[C:24]4[C:20]([N:21]=[CH:22][NH:23]4)=[C:19]([N:26]4[CH2:31][CH2:30][CH2:29][CH:28]([C:32]([O:34]CCCC)=[O:33])[CH2:27]4)[N:18]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Li+].[OH-].CC(O)=O>C1COCC1>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]3[N:25]=[C:24]4[C:20]([N:21]=[CH:22][NH:23]4)=[C:19]([N:26]4[CH2:31][CH2:30][CH2:29][CH:28]([C:32]([OH:34])=[O:33])[CH2:27]4)[N:18]=3)=[CH:14][CH:15]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium Hydroxide2×HCID 178450730HCID 178450730, compound

Product 1

HCID 178473883HCID 178473883, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of butyl 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-9H-purin-6-yl)piperidine-3-carboxylate (76 mg, 0.15 mmol) in THF (2 mL), aq. 1N LiOH (1.00 mL, 1.00 mmol) was added. The mixture was stirred at room temperature for 68 h. HOAc (1 mL) was added to neutralize LiOH. The mixture was then purified by HPLC to give 1-(2-(4-(4-acetylpiperazin-1-yl)phenylamino)-9H-purin-6-yl)piperidine-3-carboxylic acid (45 mg), MS 465.3 (M+H); UV 205.8, 272.8 nm; and 1-(2-(4-(piperazin-1-yl)phenylamino)-9H-purin-6-yl)piperidine-3-carboxylic acid (8 mg), MS 423.3 (M+H).

Workup

  1. customThe mixture was then purified by HPLC

Sources & evidence

ORD record
ord-ca20c486383244ca8708593c4a89dcb3
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

Loading…