5-Chloro-2,4-dimethoxyaniline → {1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid methyl ester

HRID 472751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472751
[CH3:1][O:2][C:3]([CH2:5][N:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:16][C:17]([OH:19])=O)[C:7]1=[O:20])=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:45][C:46]1[C:47]([O:55][CH3:56])=[CH:48][C:49]([O:53][CH3:54])=[C:50]([NH2:52])[CH:51]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.Cl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][N:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:16][C:17](=[O:19])[NH:52][C:50]2[CH:51]=[C:46]([Cl:45])[C:47]([O:55][CH3:56])=[CH:48][C:49]=2[O:53][CH3:54])[C:7]1=[O:20]

Komponenten

7

Edukt 4

HCID 668075-Chloro-2,4-dimethoxyanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68590330(3-methoxycarbonylmethyl-2-oxo-3,4-dihydro-2H-quinazolin-1-yl)-acetic acid2×

Produkt 1

HCID 68591529{1-[(5-chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2-oxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (3-methoxycarbonylmethyl-2-oxo-3,4-dihydro-2H-quinazolin-1-yl)-acetic acid (Intermediate J) (395 mg, 1.078 mmol), HATU (594 mg, 1.186 mmol) and 5-chloro-2,4-dimethoxy-phenylamine (293 mg, 1.186 mmol) in DCM (5 ml) is treated with DIPEA (2.5 eq, 618 μL). The reaction solution is stirred at RT and after 24 hours the reaction mixture is diluted with 1 M HCl (5 ml) and extracted with DCM (2×15 ml). The combined separated organic layers are washed with aqueous saturated NaHCO3. The organic phase is dried over MgSO4, filtered and is concentrated in vacuo to afford the title compound as off-white solid; [M+H]+ 448.

Aufarbeitung

  1. extractionextracted with DCM (2×15 ml)
  2. customThe combined separated organic layers
  3. washare washed with aqueous saturated NaHCO3
  4. dry with materialThe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationis concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2e79f2d3143749729b3d1d921f9dc44e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633211B2

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