Triphenylphosphine → HCID 54537267, compound

HRID 2225850Notes

Reaction equation

HRID 2225850 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:18]#[C:19][CH2:20][OH:21])[S:17][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1.[CH2:26]([O:28][C:29](=[O:39])[C:30]([C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)=[O:31])[CH3:27].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:26]([O:28][C:29](=[O:39])[C:30](=[O:31])[C:32]1[CH:37]=[CH:36][C:35]([O:21][CH2:20][C:19]#[C:18][C:16]2[S:17][C:13]3[N:12]4[C:22]([CH3:25])=[N:23][N:24]=[C:11]4[CH2:10][N:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:14]=3[CH:15]=2)=[CH:34][CH:33]=1)[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 150841353-[4-(2-Chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-2-yl]prop-2-yn-1-ol

Product 1

HCID 54537267HCID 54537267, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 15, 4-(-2-chlorophenyl)-2-(3-hydroxy-1-propynyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine (0.369 g) was reacted with 4-hydroxyphenylglyoxylic acid ethyl ester (0.195 g) in the presence of diethyl azodicarboxylate (0.175 g) and triphenylphosphine (0.263 g) in dichloromethane (30 mL). The crude reaction product, isolated in the usual manner, was purified by flash chromatography over silica gel (120 g; ethanol-dichloromethane; 3.5:96.5) to furnish 0.398 g of 4-[3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a] [1,4]diazepin-2-yl]-2-propynyloxy]-alpha-oxobenzeneacetic acid ethyl ester (4:1 ) hydrate as a white foam.

Workup

  1. customThe crude reaction product
  2. customisolated in the usual manner
  3. customwas purified by flash chromatography over silica gel (120 g; ethanol-dichloromethane; 3.5:96.5)

Sources & evidence

ORD record
ord-032a1707c72c4fef9e3b2d5d60042e11
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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