Iodoethane → N-((1R*,2R*)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-5-ethyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxamide hydrochloride

HRID 2104442Notes

Reaction equation

HRID 2104442 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][NH:27][CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2.[CH2:32](N(CC)CC)[CH3:33].C(I)C>CN(C)C=O.Cl>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([NH:14][C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[NH:20][C:21]([C:23]1[S:24][C:25]3[CH2:26][N:27]([CH2:32][CH3:33])[CH2:28][CH2:29][C:30]=3[N:31]=1)=[O:22])=[O:13])=[CH:6]2

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 68451909N-((1R*,2R)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride

Product 1

HCID 68449215N-((1R*,2R*)-2-{[(5-Chloroindol-2-yl)carbonyl]amino}-cyclopentyl)-5-ethyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (500 mg) obtained in Example 23 was dissolved in N,N-dimethylformamide (10 mL), and triethylamine (576 μl) and ethyl iodide (329 μl) were added, followed by stirring overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and water was added to the residue to collect insoluble matter by filtration. This product was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give a pale brown foamy substance. This substance was suspended in 1N hydrochloric acid (2 mL), and the suspension was concentrated under reduced pressure to give the title compound (180 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. customto collect insoluble matter
  4. filtrationby filtration
  5. customThis product was purified by silica gel column chromatography (methylene chloride:methanol=100:3)
  6. customto give a pale brown foamy substance
  7. concentrationthe suspension was concentrated under reduced pressure

Sources & evidence

ORD record
ord-458b49749bdd481bb2520077e753eeef
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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