Triethylamine → HCID 67049943, compound

HRID 2063325Notes

Reaction equation

HRID 2063325 reaction equation
CS(Cl)(=O)=O.[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([CH2:27]O)=[CH:23][CH:22]=2)=[CH:16][S:17][CH:18]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.[NH2:37][CH2:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>ClCCl.C(OCC)(=O)C.O.C(#N)C>[C:6]([O:10][C:11]([NH:13][C:14]1[C:15]([NH:19][C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([CH2:27][NH:37][CH2:38][CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[CH:23][CH:22]=2)=[CH:16][S:17][CH:18]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 61055N-(3-Aminopropyl)morpholineHCID 67049839HCID 67049839, compound

Product 1

HCID 67049943HCID 67049943, compoundYield 39%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, methanesulfonyl chloride (0.37 mL, 4.8 mmol) was added to a solution of N-(4-t-butoxycarbonylaminothiophen-3-yl)-4-hydroxymethylbenzamide (Reference Compound No. 3-2, 1.51 g, 4.3 mmol) and triethylamine (1.5 mL, 11 mmol) in anhydrous dichloromethane (70 mL), and the reaction mixture was stirred for 1.5 hours. Acetonitrile (50 mL) and N-(3-aminopropyl)morpholin (3.1 mL, 21 mmol) were added to the reaction solution and the mixture was stirred at room temperature overnight. Water (0.20 L) and ethyl acetate (0.20 L) were added to the reaction solution, and then the mixture was partitioned. The organic layer was washed with brine (0.20 L), dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to give 0.81 g of the title reference compound as yellow oil. (Yield 39%)

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with brine (0.20 L)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform-methanol)
  7. customto give 0.81 g of the title reference compound as yellow oil

Sources & evidence

ORD record
ord-96ff632d17334bb6b89e274c93ff2250
Source dataset
uspto-grants-2012_10
Patent number
US08288380B2

Reaction notes

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