tert-butyl (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetate hydrochloride → (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetic acid

HRID 640008

Reaction equation

HRID 640008 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:17][C:18]3[CH:19]=[N:20][N:21]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH:22]=3)=[N:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1>FC(F)(F)C(O)=O>[ClH:2].[Cl:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([NH:17][C:18]3[CH:19]=[N:20][N:21]([CH2:23][C:24]([OH:26])=[O:25])[CH:22]=3)=[N:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 86609386tert-butyl (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetate hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 68638745(4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetic acidYield 197.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetate hydrochloride (7.33 g, 16.1 mmol) in trifluoroacetic acid (60 ml) was stirred at room temperature for 30 minutes. The mixture was concentrated and the residue was suspended in water (120 ml), basified to pH 12 with 40% aqueous sodium hydroxide solution and then re-acidified to pH 4.8 with 2N aqueous hydrochloric acid to give (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetic acid (5.74 g, 98% yield) as a cream coloured solid:

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-6d8fccfec7c9465697b7695f5e05a15e
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Linked notes

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