Triethylamine → HCID 58294516, compound

HRID 455374Notes

Reaction equation

HRID 455374 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]2[C:19]3[CH:20]=[CH:21][C:22]([NH2:26])=[CH:23][C:24]=3[CH2:25][C@H:14]12)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]2[C:19]3[CH:20]=[CH:21][C:22]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:23][C:24]=3[CH2:25][C@H:14]12)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 58294594HCID 58294594, compound

Product 1

HCID 58294516HCID 58294516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylsulfonyl chloride (42 μL) is added to a solution of cis-7-amino-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridine-1-carboxylic acid tert-butyl ester (160 mg) and triethylamine (76 μL) in dichloromethane (3 mL) at room temperature. The solution is stirred for 1 h at room temperature and then aqueous NaHCO3 solution is added. The mixture is stirred vigorously for 20 min and then extracted with dichloromethane. The combined extract is concentrated and the residue is chromatographed (cyclohexane/ethyl acetate 7:3→1:9) to give the title compound. Yield: 120 mg (59% of theory); LC (method 1): tR=3.80 min; Mass spectrum (ESI+): m/z=365 [M−H]+.

Workup

  1. stirringThe mixture is stirred vigorously for 20 min
  2. extractionextracted with dichloromethane
  3. extractionThe combined extract
  4. concentrationis concentrated
  5. customthe residue is chromatographed (cyclohexane/ethyl acetate 7:3→1:9)

Sources & evidence

ORD record
ord-ec75cd2bff7d4db0b9df6030bff0a1a3
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Reaction notes

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