Ammonium Chloride → HCID 71258449, compound

HRID 1506214Notes

Reaction equation

HRID 1506214 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14](O)=[O:15])=[CH:12][N:11]=[C:10]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C[N:30](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.N.CO.[Cl-].[NH4+]>ClCCl>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH2:30])=[O:15])=[CH:12][N:11]=[C:10]3[N:17]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:25])[CH3:26])[CH:18]=[CH:19][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21705897Ammonia methanolHCID 58382138HCID 58382138, compound

Product 1

HCID 71258449HCID 71258449, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Cyclohexylamino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (100 mg, 0.257 mmol) in dichloromethane (2 mL) was stirred with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (10 mg, 0.052 mmol), N-hydroxybenzotriazole (50 mg, 0.37 mmol) and 7 M ammonia-methanol solution (0.2 mL, 1.4 mmol) at room temperature for one day. After addition of saturated aqueous ammonium chloride, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→0/1 (v/v)) to give the title compound as a pale yellow amorphous (71.1 mg, yield 71%).

Workup

  1. extractionthe reaction mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→0/1 (v/v))

Sources & evidence

ORD record
ord-7178b7f9e1ab4af2a72c780633917726
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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