4-Aminobenzonitrile → HCID 76741128, compound

HRID 417334Notes

Reaction equation

FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:14]([F:15])=[C:13]2[NH:16][C:17](=[O:39])[C:18]3([CH:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=4[F:30])[CH:21]([C:31](O)=[O:32])[NH:20][CH:19]3[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[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.[NH2:64][C:65]1[CH:72]=[CH:71][C:68]([C:69]#[N:70])=[CH:67][CH:66]=1>>[C:69]([C:68]1[CH:71]=[CH:72][C:65]([NH:64][C:31]([CH:21]2[NH:20][CH:19]([CH2:34][C:35]([CH3:36])([CH3:38])[CH3:37])[C:18]3([C:12]4[C:13](=[C:14]([F:15])[C:9]([Cl:8])=[CH:10][CH:11]=4)[NH:16][C:17]3=[O:39])[CH:22]2[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=2[F:30])=[O:32])=[CH:66][CH:67]=1)#[N:70]

Participants

Reactant 4

HCID 133964-Aminobenzonitrile

HCID 73910Diphenylphosphinic chloride

HCID 81531Diisopropylethylamine

HCID 86653945HCID 86653945, compound

Product 1

HCID 76741128HCID 76741128, compoundYield 33.3%

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)-7-fluoro-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid trifluoroacetic acid prepared in Example 174 (0.4 g, 0.67 mmol), was reacted with diisopropylethylamine (0.43 g, 3.4 mmol), diphenylphosphinic chloride (0.32 g, 1.3 mmol) at room temperature, then reacted with 4-aminobenzonitrile (Aldrich) (0.12 g, 1 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)-7-fluoro-2-oxo-1,2-dihydro-spiro[indole-3,3′-pyrrolidine]-5′-carboxylic acid (4-cyano-phenyl)-amide as a yellow solid (Yield 0.13 g, 33%).

Sources & evidence

ORD record: ord-0073fab177194451831e053a9ad17548
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088815B2

Reaction notes

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