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 23206Notes

Reaction equation

HRID 23206 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-66ddce0d357d4a93a76797cba7bf5cae
Source dataset
uspto-grants-2005_02
Patent number
US06849739B2

Reaction notes

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