Water → HCID 67215363, compound

HRID 2092263Notes

Reaction equation

HRID 2092263 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[O:27][CH:28]=2)[N:3]=1.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.O>C1COCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([C:26]2[O:27][CH:28]=[C:24]([CH2:23][S:22][C:4]3[C:5]([C:20]#[N:21])=[C:6]([C:10]4[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=4)[C:7]([C:8]#[N:9])=[C:2]([N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)[N:3]=3)[N:25]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 87313216HCID 87313216, compound

Product 1

HCID 67215363HCID 67215363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

80 mg (0.15 mmol) of the compound from Example 123A are initially charged in 2 ml of dry THF, and 22 mg (0.31 mmol) of pyrrolidine are added. The reaction mixture is stirred at RT for 10 h. About 2 ml of water are then added, and the mixture is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). After removal of the solvent on a rotary evaporator, the product was obtained as a white solid.

Workup

  1. customthe mixture is purified directly by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  2. customAfter removal of the solvent
  3. customon a rotary evaporator
  4. customthe product was obtained as a white solid

Sources & evidence

ORD record
ord-b4445c851d8a43369ae65b400a8fec2e
Source dataset
uspto-grants-2013_05
Patent number
US08440700B2

Reaction notes

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