Water → HCID 56943244, compound

HRID 1631137Notes

Reaction equation

HRID 1631137 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[CH:25]=O)[CH:8]=2)[N:3]=1.Cl.[CH3:32][O:33][C:34]([CH:36]1[CH2:40][CH2:39][CH2:38][NH:37]1)=[O:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl.O1CCCC1>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=3[CH2:25][N:37]3[CH2:38][CH2:39][CH2:40][CH:36]3[C:34]([O:33][CH3:32])=[O:35])[CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 12223519Methyl DL-prolinate hydrochlorideHCID 594835162-[2-Amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzaldehyde

Product 1

HCID 56943244HCID 56943244, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

500 mg of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzaldehyde are dissolved in 5 ml of 1,2-dichloroethane and 5 ml of tetrahydrofuran. 314 mg of methylpyrrolidine-2-carboxylate hydrochloride are added, and the mixture is stirred at 60° C. for 6 h. After cooling to 25° C., 566 mg of sodium triacetoxyborohydride are added and stirred at 25° C. for a further 12 h. The mixture is poured into water, extracted three times with dichloromethane, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness and purified by chromatography (reversed phase HPLC).

Workup

  1. temperatureAfter cooling to 25° C.
  2. stirringstirred at 25° C. for a further 12 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. custompurified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record
ord-a2129eb147ff4194bdb964ea182c213d
Source dataset
uspto-grants-2014_07
Patent number
US08791129B2

Reaction notes

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