Hydrochloric Acid → 2-[[3-[(1,3-benzodioxol-5-ylmethyl)(methyl)amino]propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid

HRID 434252Notes

Reaction equation

HRID 434252 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH:12](C)[CH2:13][CH2:14][N:15]([C:22]3[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]4[CH:33]=[CH:32][N:31]=[CH:30]4)[N:23]=3)[CH2:16][C:17]([O:19]CC)=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1.[Li+].[OH-].O.Cl.[CH2:39]1COCC1>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH3:39])[CH2:12][CH2:13][CH2:14][N:15]([C:22]3[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29]4[CH:33]=[CH:32][N:31]=[CH:30]4)[N:23]=3)[CH2:16][C:17]([OH:19])=[O:18])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 865863392-[[3-[(1,3-benzodioxol-5-ylmethyl)amino](methyl)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester

Product 1

HCID 224881852-[[3-[(1,3-benzodioxol-5-ylmethyl)(methyl)amino]propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid

Procedure

To 2-[[3-[(1,3-benzodioxol-5-ylmethyl)amino](methyl)propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, ethyl ester (2.2 g, 4.6 mmol) (a compound of formula (Yc10)) dissolved in THF (50 mL) was added LiOH (0.34 g, 8.1 mmol) and water (10 mL). After stirring for 16 hours, the solvent was removed in vacuo and 1 N HCl (8.1 mL, 8.1 mmol) was added. The solvent was removed in vacuo to give 2-[[3-[(1,3-benzodioxol-5-ylmethyl)(methyl)amino]propyl][2-(1H-imidazol-1-yl)-6-methyl-4-pyrimidinyl]amino]acetic acid, a compound of formula (Yc11).

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4117d7bff0c640f484c3a589579a2a73
Source dataset
uspto-grants-2003_12
Patent number
US06670473B2

Reaction notes

Loading…