Diisopropylethylamine → HCID 58474867, compound

HRID 1400867Notes

Reaction equation

HRID 1400867 reaction equation
[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:22])[C:16]([C:19]([OH:21])=O)=[CH:17][N:18]=3)[S:13][C:6]=12.[O:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][NH2:38])[CH2:32][CH2:31]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.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:22])[C:16]([C:19]([NH:38][CH2:37][CH2:36][N:33]4[CH2:34][CH2:35][O:30][CH2:31][CH2:32]4)=[O:21])=[CH:17][N:18]=3)[S:13][C:6]=12

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58207740HCID 58207740, compound

Product 1

HCID 58474867HCID 58474867, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acid 214 (180 mg, 0.434 mmol) in DMF (8 mL) was added 2-morpholinoethanamine (0.114 mL, 0.869 mmol), DIPEA (0.266 mL, 1.520 mmol) and HATU reagent (1.303 mmol). The reaction mixture was stirred at RT for 4 hr. NaHCO3 saturated solution (5 mL) and EtOAc (5 mL) were added to form a precipitate that was collected by filtration. The organic layer of the filtrate was separated, dried over anhydrous sodium sulfate, concentrated and the residue was combined with the collected precipitate to give title compound 215 (180 mg, 0.342 mmol, 79% yield) as a white solid. MS: 527.5 (MH)+.

Workup

  1. customto form a precipitate that
  2. filtrationwas collected by filtration
  3. customThe organic layer of the filtrate was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-53d1a5fd10ea47989258a945f40f6873
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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