Diisopropylethylamine → HCID 58116558, compound

HRID 661317Notes

Reaction equation

HRID 661317 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)[CH2:11][CH:10]([C:25]([OH:27])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.O[N:62]=[C:63]([O:65][CH2:66][CH3:67])[NH2:64]>CN(C)C=O>[CH2:66]([O:65][C:63]1[N:64]=[C:25]([CH:10]2[CH2:11][CH:12]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([F:24])([F:22])[F:23])=[CH:18][CH:19]=3)[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9]2)[O:27][N:62]=1)[CH3:67]

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 58116552HCID 58116552, compoundHCID 76223295ethyl N-hydroxyimidocarbamate

Product 1

HCID 58116558HCID 58116558, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 459 mg (0.889 mmol, purity 75%, 2:1 cis/trans isomer mixture) of the carboxylic acid from Example 59A in 19 ml of N,N-dimethylformamide were added, at RT, 541 mg (1.42 mmol) of HATU and 0.45 ml (337 mg, 2.61 mmol) of N,N-diisopropylethylamine, and the mixture was stirred for 30 min. Subsequently, the mixture was admixed with 136 mg (1.30 mmol) of ethyl N′-hydroxyimidocarbamate [G. Zinner, G. Nebel, Arch. Pharm. 1970, 303, 385-390] and then stirred at room temperature overnight. The reaction solution was purified directly by means of preparative HPLC. The resulting intermediate was taken up in toluene (50 ml), admixed with 4 Å molecular sieve and stirred under reflux overnight. The reaction solution was filtered, the filtrate was concentrated under reduced pressure and the residue was purified by means of preparative HPLC. Yield: 124 mg (31% of theory)

Workup

  1. customThe reaction solution was purified directly by means of preparative HPLC
  2. stirringstirred
  3. temperatureunder reflux overnight
  4. filtrationThe reaction solution was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-eedcff3883f440ed8ef55d4acf06effb
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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