HCID 18179956, compound → HCID 59077739, compound

HRID 1359890Notes

Reaction equation

HRID 1359890 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.[OH:30][C@@H:31]1[CH2:35][CH2:34][N:33]([C:36]([C:38]2[C:39]([CH3:46])=[C:40]([CH:44]=O)[NH:41][C:42]=2[CH3:43])=[O:37])[CH2:32]1>N1CCCCC1.C(O)C>[OH:30][C@@H:31]1[CH2:35][CH2:34][N:33]([C:36]([C:38]2[C:39]([CH3:46])=[C:40](/[CH:44]=[C:23]3\[C:24](=[O:29])[NH:25][C:26]4[C:22]\3=[CH:21][C:20]([S:17]([CH2:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)(=[O:19])=[O:18])=[CH:28][CH:27]=4)[NH:41][C:42]=2[CH3:43])=[O:37])[CH2:32]1

Participants

5

Reactant 2

HCID 18179956HCID 18179956, compoundHCID 88093858HCID 88093858, compound

Product 1

HCID 59077739HCID 59077739, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-[2-(2-Morpholin-4-yl-ethoxy)-phenylmethanesulfonyl]-1,3-dihydro-indol-2-one (42 mg, 0.1 mmol) was condensed with 4-((R)-3-hydroxy-pyrrolidine-1-carbonyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (24 mg, 0.1 mmol) and piperidine (1 drop) in ethanol (1.5 mL) at rt for 48 hours. The solvent was removed and the residue was purified on a silica gel column to give 44 mg (69%) of the titled compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-b2f5427d83694cb9bb70d374582b021d
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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