Formamide → Quinazoline

HRID 1803014Notes

Reaction equation

HRID 1803014 reaction equation
CO[C:3]1[CH:4]=[C:5]2[N:22]=[CH:21][N:20]=[C:19](NC3C=CC(F)=C(Cl)C=3)[C:6]2=[CH:7][C:8]=1OCCCN1CCOCC1.OC1C=C(C=CC=1OC)C#N.O1CCN(CCCCl)CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(N)=O>>[N:22]1[C:5]2[C:6](=[CH:7][CH:8]=[CH:3][CH:4]=2)[CH:19]=[N:20][CH:21]=1

Participants

6

Reactant 5

HCID 713FormamideHCID 24489Sodium DithioniteHCID 958344-(3-Chloropropyl)morpholineHCID 123631GefitinibHCID 49128223-hydroxy-4-methoxybenzonitrile2×

Product 1

HCID 9210Quinazoline

Procedure

WO 2004/024703 discloses a process for the preparation of gefitinib starting from 3-hydroxy-4-methoxy benzonitrile which involves condensation of 3-hydroxy-4-methoxy benzonitrile with morpholino propyl chloride, nitration, reduction with sodium dithionite to amino compound, hydrolysis of nitrile to amide, cyclisation in the presence of formamide to obtain quinazoline, chlorination with phosphorous oxychloride and finally condensation with chloro-fluoro aniline to obtain gefitinib. The process involves multiple steps and hence is time consuming.

Sources & evidence

ORD record
ord-03eb032aa21040a8a01c2c7707c6ff57
Source dataset
uspto-grants-2013_01
Patent number
US08350029B2

Reaction notes

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