Isopropanol → HCID 46869518, compound

HRID 578663Notes

Reaction equation

HRID 578663 reaction equation
CO[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][CH:16]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([Cl:36])[CH:31]=2)=[O:29])[CH:22]=1)[CH2:17][N:18]([CH3:20])[CH3:19])=[O:4].C1COCC1.CC(O)C.[NH4+:46].[OH-]>O>[Cl:36][C:32]1[CH:31]=[C:30]([C:28]([NH:27][C:23]2[CH:22]=[C:21]([CH:16]([NH:15][C:10]3[C:9]4[C:14](=[C:5]([C:3]([NH2:46])=[O:4])[CH:6]=[CH:7][CH:8]=4)[N:13]=[CH:12][N:11]=3)[CH2:17][N:18]([CH3:20])[CH3:19])[CH:26]=[CH:25][CH:24]=2)=[O:29])[CH:35]=[CH:34][N:33]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 86662387HCID 86662387, compound

Product 1

HCID 46869518HCID 46869518, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a 40-mL vial with magnetic stirbar at 25° C. was added 4-(1-{3-[(2-Chloro-pyridine-4-carbonyl)-amino]-phenyl}-2-dimethylamino-ethylamino)-quinazoline-8-carboxylic acid methyl ester (0.25 g, 0.495 mmol, 1 eq.) and THF (5 mL) and iPrOH (5 mL). An approx. equal volume of concentrated aq. NH4OH solution (28-30% soln.) was then added and stirring continued overnight. The reaction mixture was heated at 50° C.×4 hours in order to drive the reaction to completion. H2O (25 mL) was added to the reaction mixture and a precipitate immediately began to form. The precipitate was collected and discarded, and the aqueous layer was evaporated under nitrogen affording the desired product, 0.23 g (96% yield).

Workup

  1. customthe reaction to completion
  2. customto form
  3. customThe precipitate was collected
  4. customthe aqueous layer was evaporated under nitrogen affording the desired product, 0.23 g (96% yield)

Sources & evidence

ORD record
ord-49f6c60e325e47acbffb2aeabb904c47
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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