Triphenylphosphine → HCID 178425706, compound

HRID 2175294Notes

Reaction equation

HRID 2175294 reaction equation
[CH3:1][C:2]1[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34]O)[CH:27]=4)[CH:24]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].[C:41]([O:45][C:46]([NH:48][C:49]([NH:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[NH:50])=[O:47])([CH3:44])([CH3:43])[CH3:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[C:55]([O:54][C:52]([NH:51][C:49](=[N:48][C:46](=[O:47])[O:45][C:41]([CH3:44])([CH3:43])[CH3:42])[NH:50][CH2:34][CH2:33][O:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([CH2:25][N:23]2[CH:24]=[C:20]([C:15]3[CH:16]=[CH:17][CH:18]=[C:19]4[C:14]=3[CH2:13][CH2:12][CH2:11][N:10]4[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][O:4][C:3]3[CH:36]=[CH:37][CH:38]=[C:39]([CH3:40])[C:2]=3[CH3:1])[CH:21]=[N:22]2)[CH:27]=1)=[O:53])([CH3:58])([CH3:57])[CH3:56]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 709826674-(2,3-Dimethylphenoxy)-1-(5-(1-(3-(2-hydroxyethoxy)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-oneHCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

Product 1

HCID 178425706HCID 178425706, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2,3-dimethylphenoxy)-1-(5-(1-(3-(2-hydroxyethoxy)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one (0.02 g, 0.037 mmol), 1,3-bis(tert-butoxycarbonyl)-guanidine (0.024 g, 0.093 mmol), triphenylphosphine (0.024 g, 0.093 mmol) in DCM (0.1 mL) was added DEAD (0.040 g, 0.093 mmol, 40% wt in toluene). The reaction mixture was stirred at room temperature for 1 h and then concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.026 g, 90% yield) as a white powder. LCMS, [M+H]+=781.3.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-43c50a90ec3140c380391828b739cb92
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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