Diphenylphosphinic chloride → HCID 66624521, compound

HRID 417369Notes

Reaction equation

HRID 417369 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]([OH:32])=O)[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][O:64][C:65]([C:67]1[S:71][C:70]2[CH:72]=[CH:73][C:74]([NH2:76])=[CH:75][C:69]=2[CH:68]=1)=[O:66]>>[CH3:63][O:64][C:65]([C:67]1[S:71][C:70]2[CH:72]=[CH:73][C:74]([NH:76][C:30]([C@@H:20]3[NH:19][C@@H:18]([CH2:33][C:34]([CH3:36])([CH3:35])[CH3:37])[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])[C@H:21]3[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=3[F:29])=[O:32])=[CH:75][C:69]=2[CH:68]=1)=[O:66]

Participants

5

Reactant 4

HCID 73910Diphenylphosphinic chlorideHCID 81531DiisopropylethylamineHCID 2824064Methyl 5-amino-1-benzothiophene-2-carboxylateHCID 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 66624521HCID 66624521, compoundYield 43.3%

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 (100 mg, 0.173 mmol), was reacted with diisopropylethylamine (111 mg, 0.86 mmol), diphenylphosphinic chloride (106 mg, 0.446 mmol), then reacted with 5-Amino-benzo[b]thiophene-2-carboxylic acid methyl ester (Maybridge, 41 mg, 0.190 mmol) to give rac-5-{[(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′-carbonyl]amino}-benzo[b]thiophene-2-carboxylic acid methyl ester (49 mg, 43%). MS (ES+) m/z [(M+H)+]: 654

Sources & evidence

ORD record
ord-cdea0ddbd0d2430c889de43fe229ddd5
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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