1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 74931578, compound

HRID 1095123Notes

Reaction equation

HRID 1095123 reaction equation
Cl[C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:25]=3[O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38](O)=[O:39])=[CH:34][CH:33]=3)[C:5]2=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[NH4+:72].[Cl-:73]>CN(C)C=O>[C:38]([C:35]1[CH:34]=[CH:33][C:32]([O:31][C:25]2[CH:26]=[CH:27][C:28]([I:30])=[CH:29][C:24]=2[CH:11]2[C:10]3([C:5]4[C:6](=[CH:7][C:2]([Cl:73])=[CH:3][CH:4]=4)[NH:8][C:9]3=[O:41])[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][C:13](=[O:23])[NH:12]2)=[CH:37][CH:36]=1)(=[O:39])[NH2:72]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 74931549HCID 74931549, compound

Product 1

HCID 74931578HCID 74931578, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to the method described in Example 47a, racemic(2′R, 3R, 4′S)-6-chloro-4′-(3-chlorophenyl)-2′-[2-(4-hydroxycarbonyl-phenoxy)-5-iodo-phenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.4 g, 0.57 mmol) was reacted with EDCI (0.22 g, 1.14 mmol), HOBT (0.154 g, 1.14 mmol), diisopropylethylamine (0.29 g, 2.28 mmol), NH4Cl (60 mg, 1.14 mmol) in N,N-dimethylformamide to give racemic(2′R, 3R, 4′S)-2′-[2-(4-carbamoyl-phenoxy)-5-iodo-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.35 g, 88%)

Sources & evidence

ORD record
ord-923a9ecc54fd4a4786349391fdc4d2be
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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