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

HRID 930520Notes

Reaction equation

HRID 930520 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ca5e18a9b3744c569ec29371c9389088
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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