Diisopropylethylamine → HCID 66818428, compound

HRID 1755118Notes

Reaction equation

HRID 1755118 reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:23][CH2:22][C:21]([NH2:26])([C:24]#[N:25])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:9]([CH3:27])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([CH:43]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:45]=1)[C:40](O)=[O:41])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH: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>CN(C=O)C.C(OCC)C>[C:1]([O:5][C:6](=[O:28])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:23][CH2:22][C:21]([NH:26][C:40](=[O:41])[C:39]3[CH:43]=[C:44]([C:46]([F:48])([F:49])[F:47])[CH:45]=[C:37]([O:36][CH2:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:38]=3)([C:24]#[N:25])[CH2:20][CH2:19]2)(=[O:16])=[O:17])=[C:9]([CH3:27])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

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 21544470HCID 21544470, compoundHCID 66818590HCID 66818590, compound

Product 1

HCID 66818428HCID 66818428, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-[2-(4-Amino-4-cyano-piperidine-1-sulfonyl)-ethyl]-3-methyl-benzoic acid tert-butyl ester (500.0 mg, 1.23 mmol), 3-benzyloxy-5-trifluoromethyl-benzoic acid (436.1 mg, 1.47 mmol) and DIPEA (0.321 ml, 1.85 mmol) were dissolved in DMF (5.50 ml). HATU (561.2 mg, 1.47 mmol) was added and the mixture was stirred at room temperature for one hour. The reaction solution was diluted with diethyl ether, and the organic layer was washed with a 1 M aqueous hydrochloric acid solution, an aqueous sodium bicarbonate solution and saline. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (hexane-ethyl acetate) to give 4-{2-[4-(3-benzyloxy-5-trifluoromethyl-benzoylamino)-4-cyano-piperidine-1-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester as a yellow amorphous (796.2 mg, 94.4% in two steps).

Workup

  1. washthe organic layer was washed with a 1 M aqueous hydrochloric acid solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-aceaa2bd6d8041cfb6dc72c27c6e9421
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…