HCID 18179956, compound → HCID 59077641, compound

HRID 1359892Notes

Reaction equation

HRID 1359892 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][S:17]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][C:24](=[O:29])[CH2:23]3)(=[O:19])=[O:18])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:30][C:31]1[C:35]([C:36]([N:38]2[CH2:42][CH2:41][CH2:40][C@@H:39]2[CH2:43][N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)=[O:37])=[C:34]([CH3:49])[NH:33][C:32]=1[CH:50]=O>N1CCCCC1.C(O)C>[CH3:30][C:31]1[C:35]([C:36]([N:38]2[CH2:42][CH2:41][CH2:40][C@@H:39]2[CH2:43][N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)=[O:37])=[C:34]([CH3:49])[NH:33][C:32]=1/[CH:50]=[C:23]1\[C:24](=[O:29])[NH:25][C:26]2[C:22]\1=[CH:21][C:20]([S:17]([CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)(=[O:19])=[O:18])=[CH:28][CH:27]=2

Participants

5

Reactant 2

HCID 18179956HCID 18179956, compoundHCID 88095528HCID 88095528, compound

Product 1

HCID 59077641HCID 59077641, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-[2-(2-Morpholin-4-yl-ethoxy)-phenylmethanesulfonyl]-1,3-dihydro-indol-2-one (41 mg, 0.1 mmol) was condensed with 3,5-dimethyl-4-((R)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-1H-pyrrole-2-carbaldehyde (35 mg, 0.1 mmol) and piperidine (1 drop) in ethanol (1.5 mL) at rt for 48 hours. The solid was collected by vacuum filtration and purified on a silica gel column to give 36 mg (35%) of the titled compound.

Workup

  1. filtrationThe solid was collected by vacuum filtration
  2. custompurified on a silica gel column

Sources & evidence

ORD record
ord-4024d308c8124efe92550d0edef3f01c
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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