Diisopropylethylamine → HCID 67055921, compound

HRID 2036845Notes

Reaction equation

HRID 2036845 reaction equation
[CH3:1][C:2]1([CH3:12])[O:7][CH2:6][C:5]([CH3:11])([C:8]([OH:10])=O)[CH2:4][O:3]1.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.[NH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:48]=1[C:59]([NH2:61])=[O:60]>C(Cl)Cl>[C:59]([C:48]1[C:47]([NH:46][C:8]([C:5]2([CH3:11])[CH2:4][O:3][C:2]([CH3:1])([CH3:12])[O:7][CH2:6]2)=[O:10])=[CH:52][CH:51]=[CH:50][C:49]=1[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)(=[O:60])[NH2:61]

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 113557762,2,5-trimethyl-1,3-dioxane-5-carboxylic AcidHCID 669655723-Aminobiphenyl-2-carboxamide

Product 1

HCID 67055921HCID 67055921, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the commercially available 2,2,5-trimethyl-1,3-dioxane-5-carboxylic acid (0.6 g, 4 mmol) in DCM (30 mL) was added HATU (1.8 g, 4.7 mmol) and DIPEA (1.6 mL, 23.5 mmol). The reaction mixture was stirred at room temperature for 1 h. After this time, 3-aminobiphenyl-2-carboxamide (0.6 g, 2.35 mmol) was added and the resulting solution was stirred for 16 h. At the conclusion of this period, the reaction mixture was washed with water, dried, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (25% ethyl acetate in hexanes) to yield N-(2-carbamoylbiphenyl-3-yl)-2,2,5-trimethyl-1,3-dioxane-5-carboxamide (0.25 g, 24% yield) as a white solid. LCMS Method Y: retention time 1.69 min; [M+1]=367.2.

Workup

  1. stirringthe resulting solution was stirred for 16 h
  2. washAt the conclusion of this period, the reaction mixture was washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6ac0517f75c446a7b0a09517b67fe7ac
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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