Diphenylphosphinic chloride → HCID 75985873, compound

HRID 417299Notes

Reaction equation

HRID 417299 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[C:13]2[NH:15][C:16](=[O:38])[C:17]3([CH:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=4[F:29])[CH:20]([C:30](O)=[O:31])[NH:19][CH:18]3[CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:12]2=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:63][CH:64]1[CH2:69][N:68]([C:70]2[CH:76]=[CH:75][C:73]([NH2:74])=[C:72]([O:77][CH3:78])[CH:71]=2)[CH2:67][CH:66]([CH3:79])[O:65]1>>[CH3:63][CH:64]1[O:65][CH:66]([CH3:79])[CH2:67][N:68]([C:70]2[CH:76]=[CH:75][C:73]([NH:74][C:30]([CH:20]3[NH:19][CH:18]([CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:17]4([C:12]5[C:13](=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=5)[NH:15][C:16]4=[O:38])[CH:21]3[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=3[F:29])=[O:31])=[C:72]([O:77][CH3:78])[CH:71]=2)[CH2:69]1

Participants

5

Reactant 4

HCID 73910Diphenylphosphinic chlorideHCID 81531DiisopropylethylamineHCID 455884204-(2,6-Dimethylmorpholin-4-yl)-2-methoxyanilineHCID 78158843rac-(2'R,3'S,4'S,5'R)-6-chloro-4'-(3-chloro-2-fluoro-phenyl)-2'-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid trifluoroacetic acid

Product 1

HCID 75985873HCID 75985873, compoundYield 37.4%

Procedure

In a manner similar to the method described in Example 5, rac-(2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid trifluoroacetic acid prepared in Example 4 (0.25 g, 0.43 mmol), was reacted with diisopropylethylamine (0.29 g, 2.2 mmol), diphenylphosphinic chloride (0.21 g, 0.89 mmol), then reacted with 4-(2,6-dimethylmorpholino)-2-methoxyaniline (Bionet) (0.11 g, 0.44 mmol) to give rac-(2′S,3′R,4′S,5′R)-6-chloro-4′-(3-chloro-2-fluoro-phenyl)-2′-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid [4-(2,6-dimethyl-morpholin-4-yl)-2-methoxy-phenyl]-amide as a white solid (Yield 0.11 g, 37%).

Sources & evidence

ORD record
ord-c712389b95d44b0db13e2e84810c7803
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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