Diisopropylethylamine → HCID 118509711, compound

HRID 1487273Notes

Reaction equation

HRID 1487273 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.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.[NH2:46][C:47]1[CH:48]=[C:49]2[C:53](=[CH:54][C:55]=1[NH:56][C@@H:57]([CH3:61])[CH2:58][O:59][CH3:60])[N:52]([CH3:62])[C:51](=[O:63])[C:50]2([CH3:65])[CH3:64]>CN1C(=O)CCC1>[CH3:60][O:59][CH2:58][C@@H:57]([NH:56][C:55]1[CH:54]=[C:53]2[C:49]([C:50]([CH3:65])([CH3:64])[C:51](=[O:63])[N:52]2[CH3:62])=[CH:48][C:47]=1[NH:46][C:10]([C:4]1[CH:5]=[C:6]([CH3:9])[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1)=[O:12])[CH3:61]

Participants

6

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 118065045HCID 118065045, compound

Product 1

HCID 118509711HCID 118509711, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid D1 (47 mg; 0.28 mmol), is dissolved in NMP (500 μl) and DIPEA (135 μl; 0.85 mmol) and HATU (111 mg; 0.29 mmol) is added. The reaction mixture is stirred at ambient temperature for 15 min. 5-Amino-6-((S)-2-methoxy-1-methyl-ethylamino)-1,3,3-trimethyl-1,3-dihydro-indol-2-one E-1.1 (85 mg; 0.31 mmol) dissolved in NMP (500 μl) is added and stirring is continued for 12 h at ambient temperature. The reaction mixture is poured on water and extracted with DCM once. The organic phase is dried with MgSO4 and concentrated under reduced pressure.

Workup

  1. additionis added
  2. stirringstirring
  3. waitis continued for 12 h at ambient temperature
  4. additionThe reaction mixture is poured on water
  5. extractionextracted with DCM once
  6. dry with materialThe organic phase is dried with MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f3a5e58f99b4b7d81be17709cb5080d
Source dataset
uspto-grants-2016_08
Patent number
US09428515B2

Reaction notes

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