Methyl-{3-[4-(2-pyridin-2-yl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-carbamic acid tert-butyl ester → HCID 10135569, compound

HRID 8273Notes

Reaction equation

HRID 8273 reaction equation
C(O[C:6](=O)[N:7](C)[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([C:22]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)=[N:25][N:24]4[CH2:33][CH2:34][CH2:35][C:23]=34)=[CH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1)(C)(C)C>FC(F)(F)C(O)=O>[CH3:6][NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([C:22]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)=[N:25][N:24]4[CH2:33][CH2:34][CH2:35][C:23]=34)=[CH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 69365909Methyl-{3-[4-(2-pyridin-2-yl-5,6-dihydro-4h-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 10135569HCID 10135569, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl-{3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxy]-propyl}-carbamic acid tert-butyl ester (100 mg, 0.2 mmol) in trifluoracetic acid (3 mL) is stirred at room temperature for 6 h. The mixture is concentrated in vacuo and traces of trifluoroacetic acid removed by repeated evaporation with chloroform. The residue is placed on an SCX column and washed with water, methanol, and 7 N ammonia in methanol. Concentration of the appropriate fraction yields the title compound, 40 mg (50%), as yellow oil.

Workup

  1. concentrationThe mixture is concentrated in vacuo and traces of trifluoroacetic acid
  2. customremoved
  3. customevaporation with chloroform
  4. washwashed with water, methanol, and 7 N ammonia in methanol

Sources & evidence

ORD record
ord-83d42c16ddd347fe8030d060c09fb854
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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