Hydrochloric Acid → HCID 11754658, compound

HRID 1788333Notes

Reaction equation

HRID 1788333 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:27][CH:26]=4)=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.Cl.[CH3:37]O>>[CH3:37][O:34][C:33](=[O:35])[CH2:32][CH2:31][C:28]1[CH:27]=[CH:26][C:25]([C:21]2[CH:20]=[C:19]3[C:24]([C:15]([C:8]4[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)=[N:11][N:10]5[CH2:12][CH2:13][CH2:14][C:9]=45)=[CH:16][CH:17]=[N:18]3)=[CH:23][CH:22]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 69060315HCID 69060315, compound

Product 1

HCID 11754658HCID 11754658, compound

Procedure

Into a 100 mL roundbottom flask is placed 3-{4-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl]phenyl}propionic Acid (Example 30 before reverse phase purification) (160 mg, 0.35 mmol), 20 mL of MeOH, and 1.5 mL of conc HCl solution. The mixture is refluxed 3 h, and solvent removed under reduced pressure. The product is partitioned between CH2Cl2 (20 mL) and saturated K2CO3 solution. The organic layer is collected and dried (MgSO4) and concentrated under vacuum. The title compound, 88.4 mg (54%), is crystallized from a concentrated CH2Cl2-Hexanes mixture.

Workup

  1. customInto a 100 mL roundbottom flask is placed
  2. temperatureThe mixture is refluxed 3 h
  3. customsolvent removed under reduced pressure
  4. customThe product is partitioned between CH2Cl2 (20 mL) and saturated K2CO3 solution
  5. customThe organic layer is collected
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under vacuum
  8. customThe title compound, 88.4 mg (54%), is crystallized from a concentrated CH2Cl2-Hexanes mixture

Sources & evidence

ORD record
ord-d53f2e58c9774e8984be8aeaf795a267
Source dataset
uspto-grants-2009_03
Patent number
US07511065B2

Reaction notes

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