Diisopropylethylamine → {3-Benzylamino-4-[(1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

HRID 930520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 930520
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][C:4]([C:10]([OH:12])=O)=[CH:3]1.[C:13]([O:17][C:18](=[O:35])[NH:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:21]=1)([CH3:16])([CH3:15])[CH3:14].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.O>[C:13]([O:17][C:18](=[O:35])[NH:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:10]([C:4]2[CH:5]=[C:6]([CH3:9])[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=2)=[O:12])=[C:22]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:21]=1)([CH3:16])([CH3:14])[CH3:15]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218859251,5-Dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidHCID 117889326(4-Amino-3-benzylamino-phenyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 117894045{3-Benzylamino-4-[(1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid D1 (5.000 g; 16 mmol) and (4-Amino-3-benzylamino-phenyl)-carbamic acid tert-butyl ester E-1.5 (3.200 g; 19 mmol) are dissolved in THF and and cooled to 0° C. DIPEA (6.186 g; 48 mmol) is then added, the mixture is stirred for 15 min Finally HATU (12.133 g; 32 mmol) is added. The mixture is stirred at room temperature for 1 hr. The reaction is diluted with water and extracted with MeOH/DCM. The combined organic layer is dried over Na2SO4 and concentrated in vacuum. The residue is used in the next step without further purification.

Aufarbeitung

  1. additionis added
  2. extractionextracted with MeOH/DCM
  3. dry with materialThe combined organic layer is dried over Na2SO4
  4. concentrationconcentrated in vacuum
  5. customThe residue is used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ca5e18a9b3744c569ec29371c9389088
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296748B2

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