1-Pyrrolidineethanamine → HCID 74931454, compound

HRID 1095103Notes

Reaction equation

HRID 1095103 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39](F)=[O:40])=[CH:35][CH:34]=2)=[C:6]([CH:8]2[C:13]3([C:21]4[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=4)[NH:15][C:14]3=[O:23])[CH:12]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH2:11][C:10](=[O:31])[NH:9]2)[CH:7]=1.[NH2:42][CH2:43][CH2:44][N:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1.CN1CCOCC1>CN(C)C1C=CN=CC=1.O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39](=[O:40])[NH:42][CH2:43][CH2:44][N:45]3[CH2:49][CH2:48][CH2:47][CH2:46]3)=[CH:35][CH:34]=2)=[C:6]([CH:8]2[C:13]3([C:21]4[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=4)[NH:15][C:14]3=[O:23])[CH:12]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH2:11][C:10](=[O:31])[NH:9]2)[CH:7]=1

Participants

6

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 79724-MethylmorpholineHCID 74931420HCID 74931420, compound

Product 1

HCID 74931454HCID 74931454, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 55b, racemic(2′R, 3R, 4′S)-2′-[5-bromo-2-(4-fluorocarbonyl-phenoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.18 g, 0.28 mmol) was reacted with N-(2-aminoethyl)pyrrolidine (0.4 g, 3.5 mmol), N-methylmorpholine and 4-dimethylaminopyridine in tetrahydrofuran to give racemic(2′R, 3R, 4′S)-2′-{5-bromo-2-[4-(2-pyrrolidin-1-yl-ethylcarbamoyl)-phenoxy]-phenyl}-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.17 g, 83%).

Sources & evidence

ORD record
ord-277463001f5c416e8b9e67ad294797d7
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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