Acetic Anhydride → 5-[2-(Acetylamino)ethyl]-N-((1R*,2S*)-2-{[(5-chloroindol-2-yl)carbonyl]amino}cyclohexyl)-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine-2-carboxamide Hydrochloride

HRID 2104445Notes

Reaction equation

HRID 2104445 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[N:11]=[C:12]([C:14]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]3[NH:23][C:24]([C:26]3[NH:27][C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([Cl:35])=[CH:30][CH:29]=4)=[O:25])=[O:15])[S:13][C:7]=2[CH2:6]1.C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44]>CN(C)C=O.Cl>[ClH:35].[C:43]([NH:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[N:11]=[C:12]([C:14]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]3[NH:23][C:24]([C:26]3[NH:27][C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([Cl:35])=[CH:30][CH:29]=4)=[O:25])=[O:15])[S:13][C:7]=2[CH2:6]1)(=[O:45])[CH3:44]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67056679HCID 67056679, compound

Product 1

HCID 670566145-[2-(Acetylamino)ethyl]-N-((1R*,2S*)-2-{[(5-chloroindol-2-yl)carbonyl]amino}cyclohexyl)-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridine-2-carboxamide Hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (90 mg) obtained in Example 40 was dissolved in N,N-dimethylformamide (3 mL), triethylamine (65 μl) and acetic anhydride (22 μl) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and methylene chloride and 0.3N aqueous sodium hydroxide were added to the residue for partitioning the mixture. The resultant organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3) to give a colorless foamy substance. This product was suspended in 1N hydrochloric acid (0.3 mL), and the suspension was concentrated under reduced pressure to give the title compound (73 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride and 0.3N aqueous sodium hydroxide
  2. additionwere added to the residue
  3. customfor partitioning the mixture
  4. dry with materialThe resultant organic layer was dried over sodium sulfate anhydrate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=100:3)
  7. customto give a colorless foamy substance
  8. concentrationthe suspension was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27856092a526400986e739681526958a
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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