Diisopropylethylamine → HCID 58116486, compound

HRID 661312Notes

Reaction equation

HRID 661312 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][N:14]([C:16]([N:18]3[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]3)=[O:17])[CH2:13][CH:12]([C:26](O)=[O:27])[CH2:11]2)=[CH:6][CH:5]=1.O[N:31]=[C:32]([O:34][CH2:35][CH3:36])[NH2:33].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>CN(C=O)C>[F:1][CH:2]([F:29])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][CH:12]([C:26]3[O:27][N:33]=[C:32]([O:34][CH2:35][CH3:36])[N:31]=3)[CH2:13][N:14]([C:16]([N:18]3[CH2:19][CH2:20][S:21](=[O:25])(=[O:24])[CH2:22][CH2:23]3)=[O:17])[CH2:15]2)=[CH:8][CH:9]=1

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 581165675-[4-(Difluoromethoxy)phenyl]-1-[(1,1-dioxidothiomorpholin-4-yl)carbonyl]piperidine-3-carboxylic acidHCID 76223295ethyl N-hydroxyimidocarbamate

Product 1

HCID 58116486HCID 58116486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

226 mg (0.52 mmol) of the compound from Example 40A and 109 mg (1.05 mmol) of ethyl N′-hydroxyimidocarbamate [G. Zinner, G. Nebel, Arch. Pharm. 1970, 303, 385-390] were initially charged in 2.0 ml of DMF and reacted with 298 mg (0.8 mmol) of HATU and 0.27 ml (203 mg, 1.6 mmol) of N,N-diisopropylethylamine. The mixture was stirred at RT for 15 minutes and then the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed repeatedly with water, dried over sodium sulphate and concentrated under reduced pressure. The residue was taken up in 5.0 ml of dioxane and admixed with about 1 g of 4 Å molecular sieve. The mixture was heated to reflux for 16 h, and the reaction mixture was purified by means of preparative HPLC. Yield: 86 mg (30% of theory)

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic phase was washed repeatedly with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 16 h
  7. customthe reaction mixture was purified by means of preparative HPLC

Sources & evidence

ORD record
ord-a8c6190be6844638b26d23e334cddd8b
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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