Sodium Hydroxide → (2R)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoic acid

HRID 1162203Notes

Reaction equation

HRID 1162203 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[O:28][C@H:29]([CH3:34])[C:30]([O:32]C)=[O:31])[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[O:28][C@H:29]([CH3:34])[C:30]([OH:32])=[O:31])[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86627834methyl (2R)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate

Product 1

HCID 68618787(2R)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl (2R)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (520 mg, 1.15 mmol) (obtained as described in example 1, preparation of starting materials) in methanol (10 ml), was added 2.5M aqueous sodium hydroxide (2 ml, 5 mmol) and the solution was stirred for 3 hours. The solution was evaporated and the residue was taken into water and was acidified to about pH4 with acetic acid and stirred for 15 minutes. The precipitate was filtered off, washed with water and dried to provide (2R)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoic acid, (435 mg, 86%); NMR spectrum (300 MHz) 1.69 (d, 3H), 5.36 (q, 1H), 5.75 (s, 2H), 6.94 (d, 1H), 7.14 (d, 1H), 7.27 (t, 1H), 7.35 (d, 1H), 7.71 (m, 4H), 8.12 (s, 1H), 8.43 (s, 1H), 8.52 (s, 2H), 10 76 (s, 1H), one exchangeable not observed; Mass spectrum MH+ 441.

Workup

  1. customThe solution was evaporated
  2. stirringstirred for 15 minutes
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-749c1d88050a4ff08045b1d927cf204b
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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