Triethylamine → HCID 66671646, compound

HRID 446574Notes

Reaction equation

HRID 446574 reaction equation
[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:43])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([C:20](=[O:42])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:41])[N:34]([CH2:36][CH2:37][CH2:38][CH2:39]O)[CH3:35])=[CH:29][CH:28]=2)[CH3:19])[CH2:12][CH2:11]1.[CH2:50]([N:52](CC)CC)C.CS(Cl)(=O)=O.CN.CO>ClCCl>[C:1]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:43])[O:9][CH:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][N:18]([CH3:19])[C:20](=[O:42])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:41])[N:34]([CH3:35])[CH2:36][CH2:37][CH2:38][CH2:39][NH:52][CH3:50])=[CH:29][CH:28]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 57454252Monomethylamine methanolHCID 66671454HCID 66671454, compound

Product 1

HCID 66671646HCID 66671646, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (107 mg, 0.159 mmol) obtained in Example 80a was dissolved in dichloromethane (6 mL), triethylamine (0.044 mL, 0.32 mmol) and methanesulfonyl chloride (0.018 mL, 0.24 mmol) were added under ice cooling, and the mixture was stirred at the same temperature for 10 minutes. Triethylamine (0.044 mL, 0.32 mmol) and methanesulfonyl chloride (0.018 mL, 0.24 mmol) were further added under ice cooling, then a 40% methyl amine-methanol solution (6 mL) was added, and the mixture was stirred at room temperature for 14 hours. After the reaction was completed, the solvent was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (elution solvents, n-hexane:ethyl acetate:methanol=1:1:0→0:1:0→0:9:1, v/v/v) to give the title compound (84 mg; yield, 77%) as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. customthe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by NH silica gel column chromatography (elution solvents, n-hexane:ethyl acetate:methanol=1:1:0→0:1:0→0:9:1, v/v/v)

Sources & evidence

ORD record
ord-6f2514f401154c9983ce1bd8ac98251a
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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