Diisopropylethylamine → HCID 67432901, compound

HRID 2036630Notes

Reaction equation

HRID 2036630 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[NH:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:18]([C:20](O)=[O:21])[CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C.O>[C:26]([O:25][C:23](=[O:24])[NH:17][CH:18]([C:20](=[O:21])[NH:16][C:11]1[C:10]([NH:9][C:4]2[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=2)=[CH:15][CH:14]=[CH:13][N:12]=1)[CH3:19])([CH3:27])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67434521HCID 67434521, compound

Product 1

HCID 67432901HCID 67432901, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

N3-(3,5-Difluorophenyl)-pyridine-2,3-diamine (750 mg, 3.39 mmol), Boc-L-Ala-OH (640 mg, 3.39 mmol) and HATU (2.57 g, 6.78 mmol) were suspended in DCM-DMF (1:1) (10.2 mL). DIEA (874.6 mg, 6.78 mmol) was added to reaction mixture and stirred at rt for 8 h. After completion, the reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-10% MeOH in DCM to provide {1-[3-(3,5-difluorophenylamino)-pyridin-2-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester: LC-MS (ESI) m/z 393.2 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-278e5758eff94390b2bd10b187e1bb27
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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