Sodium Hydroxide → HCID 21104324, compound

HRID 1354325Notes

Reaction equation

HRID 1354325 reaction equation
C([O:3][C:4](=[O:30])[C:5]1[C:10]([NH:11][C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[N:15]=[C:14]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=3[F:29])[N:13]=2)=[CH:9][CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+]>CO>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]([F:29])=[C:22]([C:14]2[N:13]=[C:12]([NH:11][C:10]3[C:5]([C:4]([OH:30])=[O:3])=[CH:6][N:7]=[CH:8][CH:9]=3)[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[N:15]=2)[CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58865951HCID 58865951, compound

Product 1

HCID 21104324HCID 21104324, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-[2-(5-chloro-2-fluorophenyl)-5,6,7,8-tetrahydroquinazolin-4-ylamino]-nicotinic acid ethyl ester (150 mg, 0.35 mmol, 1 eq) in MeOH (5 ml) was added a 1N NaOH(aq) solution (423 μl, 0.42 mmol, 1.2 eq) and the reaction mixture was refluxed for 1 h. The solution was cooled to rt and concentrated in vacuo. Water (20 ml) was added to the crude material and the aqueous layer was acidified to pH 4. The solid was filtered, washed with water (2×5 ml) and dried overnight to give 4-[2-(5-chloro-2-fluorophenyl)-5,6,7,8-tetrahydroquinazolin-4-ylamino]-nicotinic acid, 50 (132 mg, 94%) as a cream colored solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 1 h
  2. concentrationconcentrated in vacuo
  3. additionWater (20 ml) was added to the crude material
  4. filtrationThe solid was filtered
  5. washwashed with water (2×5 ml)
  6. customdried overnight

Sources & evidence

ORD record
ord-6dbf67118c4f4aa9bf8ee2fe02d764cf
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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