Isopropanol → HCID 86662385, compound

HRID 578658Notes

Reaction equation

HRID 578658 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:31]=[CH:30][N:29]=[C:28]([Cl:32])[CH:27]=2)=[O:25])[CH:18]=1)=O.C1COCC1.CC(O)C.[OH-].[NH4+:43]>O>[Cl:32][C:28]1[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]([NH2:43])=[O:2])[CH:6]=[CH:7][CH:8]=3)[N:13]=[CH:12][N:11]=2)=[O:25])[CH:31]=[CH:30][N:29]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 86662386HCID 86662386, compound

Product 1

HCID 86662385HCID 86662385, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 40-mL vial with magnetic stirbar at r.t. was added the 4-{3-[(2-Chloro-pyridine-4-carbonyl)-amino]-benzylamino}-quinazoline-8-carboxylic acid methyl ester (0.6 g, 1.34 mmol, 1 eq.) and THF (6 mL) and 2-propanol (6 mL). An approx. equal volume (i.e.; 6 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 white precipitate immediately began to form. The precipitate was collected and dried thoroughly in vacuo and afforded 314 mg (55% yield). Material was carried on to the next synthetic step without further purification. LCMS (ESI) 433 (M+H)

Workup

  1. customto form
  2. customThe precipitate was collected
  3. customdried thoroughly in vacuo
  4. customafforded 314 mg (55% yield)
  5. customMaterial was carried on to the next synthetic step without further purification

Sources & evidence

ORD record
ord-92aba74e2bf141a89e26482907c2a863
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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