N-(2-aminoethyl)acetamide → 4'-{2-[1-(2-acetylamino-ethylcarbamoyl)-1-methyl-ethoxy]-5-chloro-phenyl}-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504445Notes

Reaction equation

HRID 504445 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:38])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])[CH2:14][C:13](=[O:29])[NH:12][CH:11]3[C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[CH3:37])[C:5]2=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:70][CH2:71][CH2:72][NH:73][C:74](=[O:76])[CH3:75]>C1COCC1>[C:74]([NH:73][CH2:72][CH2:71][NH:70][C:25]([C:24]([CH3:28])([O:23][C:17]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=1[CH:15]1[CH2:14][C:13](=[O:29])[NH:12][CH:11]([C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[CH3:37])[C:10]21[C:5]1[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[NH:8][C:9]2=[O:38])[CH3:27])=[O:26])(=[O:76])[CH3:75]

Participants

7

Reactant 5

HCID 66082N-(2-aminoethyl)acetamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 765678856-chloro-4'-[5-chloro-2-(2-hydroxy-1,1-dimethyl-ethoxy)phenyl]-2'-[5-fluoro-2-methylphenyl]spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 749286864'-{2-[1-(2-acetylamino-ethylcarbamoyl)-1-methyl-ethoxy]-5-chloro-phenyl}-6-chloro-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(2-hydroxy-1,1-dimethyl-ethoxy)-phenyl]-2′-[5-fluoro-2-methylphenyl]-spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (35 mg, 0.06 mmol), EDCl (18 mg, 0.094 mmol), HOBt (14 mg, 0.094 mmol) and DIPEA (23 mg, 0.2 mmol) in THF (2 mL) was added N-(2-amino-ethyl)-acetamide (19 mg, 0.18 mmol). The mixture was stirred at room temperature overnight, purified by prep-HPLC to give the title compound as a white solid (11 mg).

Workup

  1. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-86da85f4a232440aae9d4344823eddac
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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