Isopropanol → HCID 66763406, compound

HRID 578673Notes

Reaction equation

HRID 578673 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][N:11]=[C:10]2[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24]([C:26]2[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)=[O:25])[CH:18]=1)=O.C1COCC1.CC(O)C.[OH-].[NH4+:44]>O>[CH3:33][O:32][C:29]1[N:28]=[CH:27][C:26]([C:24]([NH:23][C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=2)[CH2:16][NH:15][C:10]2[C:9]3[C:14](=[C:5]([C:3]([NH2:44])=[O:2])[CH:6]=[CH:7][CH:8]=3)[N:13]=[CH:12][N:11]=2)=[O:25])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 66763627HCID 66763627, compound

Product 1

HCID 66763406HCID 66763406, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 40-mL vial with magnetic stirbar at 25° C. was added 4-{3-[(6-Methoxy-pyridine-3-carbonyl)-amino]-benzylamino}-quinazoline-8-carboxylic acid methyl ester (0.18 g, 0.4 mmol, 1 eq.) and THF (2 mL) and 2-propanol (2 mL). An approx. equal volume (i.e.; 2 mL) of concentrated aqueous ammonium hydroxide solution (28-30% soln.) was then added and stirring continued overnight. Water (15 mL) was added to the reaction mixture and a precipitate immediately began to form. The precipitate was collected and purified further via preparative HPLC afforded the desired compound as a white solid (13.9 mg) LCMS (ESI) 429.2 (M+H).

Workup

  1. customto form
  2. customThe precipitate was collected
  3. custompurified further via preparative HPLC

Sources & evidence

ORD record
ord-b632a48e6ac24bbf8dcf8f1255c346cf
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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