Hydrochloric Acid → {4-[6-(2-Piperidin-4-yl-(E)-vinyl)-1H-indazol-3-yl]-piperidin-1-yl}-acetic acid, hydrochloride hydrate

HRID 343408Notes

Reaction equation

HRID 343408 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4](/[CH:7]=[CH:8]/[C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH:18]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]4)=[N:14][NH:15]3)=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.[ClH:28]>O>[OH2:26].[ClH:28].[NH:1]1[CH2:6][CH2:5][CH:4](/[CH:7]=[CH:8]/[C:9]2[CH:17]=[C:16]3[C:12]([C:13]([CH:18]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]4)=[N:14][NH:15]3)=[CH:11][CH:10]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178525827HCID 178525827, compound

Product 1

HCID 178479771{4-[6-(2-Piperidin-4-yl-(E)-vinyl)-1H-indazol-3-yl]-piperidin-1-yl}-acetic acid, hydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of {4-[6-(2-piperidin-4-yl-(E)-vinyl)-1H-indazol-3-yl]-piperidin-1-yl}-acetic acid (20.5 g) in water (41 ml) was carefully adjusted to pH 5.7 with 2M hydrochloric acid (27 ml). The resulting solution was filtered through 1 micron graded glass fibre filter paper and the filter washed through with water (2×20.5 ml). Isopropanol (219 ml) was added dropwise to the stirred filtrate over 0.25 h at 22°, and the solution was seeded with product crystals (10 mg). The mixture was allowed to crystallise for 0.5 h, stirred at 22° for 1.5 h, and further isopropanol (219 ml) was added slowly over 0.5 h. After stirring for a further 3 h at 22° the suspension was filtered. The filter cake was washed with a mixture of isopropanol:water (4:1, 2×41 ml) and dried in vacuo at 45° for 6 h to give the title compound as a white solid (14.1 g).

Workup

  1. filtrationThe resulting solution was filtered through 1 micron
  2. washthe filter washed through with water (2×20.5 ml)
  3. additionIsopropanol (219 ml) was added dropwise to the stirred filtrate over 0.25 h at 22°
  4. customto crystallise for 0.5 h
  5. additionfurther isopropanol (219 ml) was added slowly over 0.5 h
  6. stirringAfter stirring for a further 3 h at 22° the suspension
  7. filtrationwas filtered
  8. washThe filter cake was washed with a mixture of isopropanol:water (4:1, 2×41 ml)
  9. customdried in vacuo at 45° for 6 h

Sources & evidence

ORD record
ord-ac1513bd9b0540f08be82064e364eb16
Source dataset
uspto-grants-1999_01
Patent number
US05861414

Reaction notes

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