Triethylamine → HCID 58189123, compound

HRID 1423128Notes

Reaction equation

HRID 1423128 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:28])[F:27])=[N:19]3)[CH2:11][CH2:10][N:9]1[CH2:30][C:31]([OH:33])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:35]([O:38][NH2:39])[CH:36]=[CH2:37].C(N(CC)CC)C.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:35]([O:38][NH:39][C:31](=[O:33])[CH2:30][N:9]1[CH2:10][CH2:11][N:12]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:27])([F:28])[F:29])=[N:19]3)[CH2:13][C@@H:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:36]=[CH2:37]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 58189026HCID 58189026, compound

Product 1

HCID 58189123HCID 58189123, compoundYield 68.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-2-(2-benzyl-4-(8-methoxy-2-(trifluoromethyl)quinolin-5-yl)piperazin-1-yl)acetic acid (115 mg, 0.25 mmol) in CH2Cl2 (2 mL) at 0-5° C. was treated with O-allylhydroxylamine hydrochloride (31 mg, 0.28 mmol), triethylamine (38 μL, 0.28 mmol), catalytic DMAP, and finally DCC (57 mg, 0.28 mmol). The reaction mixture was stirred for 3 h after which time the mixture was treated with EtOAc (5 mL), filtered and evaporated. The residue was purified by silica gel flash chromatography with 50% EtOAc/hexane, then 100% EtOAc, as eluant to afford the title compound as an oil (88 mg, 68%). LC/MS (Method A) 5.66 min, [M+1]+ 515.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by silica gel flash chromatography with 50% EtOAc/hexane

Sources & evidence

ORD record
ord-088caf06f36e4e7f8eaefa19ad73e8c6
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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