Hydrochloric Acid → 1-(4-(5-Bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylic acid

HRID 2067872Notes

Reaction equation

HRID 2067872 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:26]=[CH:25][C:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([C:21]([O:23]C)=[O:22])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[Li+].[OH-].Cl.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CO.O.C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:26]=[CH:25][C:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 24436Sodium SulfateHCID 68727496Methyl 1-(4-(5-bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylate

Product 1

HCID 585422801-(4-(5-Bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Crude methyl 1-(4-(5-bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylate 20 is suspended in THF/MeOH/H2O (3:2:1, 10 mL) and 6N LiOH (9.3 mmol) and stirred at rt for 2 h. After neutralization to pH 6 by addition of HCl (1N), the solvent is removed under vacuum to give a solid which is dissolved in THF (20 mL). To the above suspension, excess Na2SO4 is added and filtered. The filtrate is concentrated to yield 1-(4-(5-bromopyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylic acid 21. 1H NMR (400 MHz, d6-DMSO) δ 9.87 (s, 1H), 9.39 (bs, 1H), 8.59 (s, 2H), 7.66 (d, J=8.4 Hz, 2H), 7.20 (d, J=8.4 Hz, 2H), 3.58-3.64 (m, 2H), 3.48-3.28 (m, 1H), 3.22-3.27 (m, 2H), 2.88-3.03 (m, 4H), 2.05-2.15 (m, 2H), 1.66-1.80 (m, 2H). MS (m/z) (M+1)+: 405.1, 407.1.

Workup

  1. customthe solvent is removed under vacuum
  2. customto give a solid which
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-e8548e37ec0a4ae6a66fb69268314631
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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