Dichloromethane → Quinazoline hydrochloride

HRID 2182562Notes

Reaction equation

HRID 2182562 reaction equation
BrC1C=CC([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13](O)=[C:14](OC)[CH:15]=3)[N:10]=[CH:9]C=2)=C(F)C=1.OCCCN1CCCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(Cl)[Cl:65]>>[ClH:65].[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[N:6][CH:9]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5667441-(3-Hydroxypropyl)pyrrolidin-2-oneHCID 1364116824-(4-Bromo-2-fluoroanilino)7-hydroxy-6-methoxyquinoline

Product 1

HCID 21186983Quinazoline hydrochlorideYield 67%

Procedure

Using a method analogous to that in Example 47, 4-(4-bromo-2-fluoroanilino)7-hydroxy-6-methoxyquinoline (146 mg, 0. mmol) in methylene chloride (5 ml) was treated with 1-(3hydroxypropyl)-2-pyrrolidinone (86 mg, 0.6 mmol), triphenylphosphine (314 mg, 1.2 mmol) and diethyl azodicarboxylate (209 mg, 1.2 mmol) and was purified and isolated to give 4-(4-bromo-2-fluoroanilino)-methoxy-73(oxopyrrolidin-1-yl)propoxy)quinazoline hydrochloride (140 mg, 67%).

Workup

  1. customwas purified
  2. customisolated

Sources & evidence

ORD record
ord-33fcd66a73d04b5bb83ca849b9eeb3f2
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

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