Triethylamine → HCID 67248225, compound

HRID 2273189Notes

Reaction equation

HRID 2273189 reaction equation
CS(Cl)(=O)=O.[CH2:6]([O:8][C:9]([CH:11]1[CH:24](O)[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:26][CH3:27])[CH:21]=3)[N:16]=[CH:15][C:14]=2[S:13][CH2:12]1)=[O:10])[CH3:7].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1>[CH2:6]([O:8][C:9]([C:11]1[CH2:12][S:13][C:14]2[CH:15]=[N:16][C:17]3[C:22]([C:23]=2[CH:24]=1)=[CH:21][C:20]([O:26][CH3:27])=[CH:19][CH:18]=3)=[O:10])[CH3:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 67247001HCID 67247001, compound

Product 1

HCID 67248225HCID 67248225, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (745 μL, 9.63 mmol, 3.0 eq) is added at room temperature to a stirred solution of 4-hydroxy-6-methoxy-3,4-dihydro-2H-1-thia-9-aza-phenanthrene-3-carboxylic acid ethyl ester (1.02 g, 3.21 mmol, 1.0 eq) in dichloromethane (10 mL), followed by triethylamine (2.23 mL, 16.05 mmol, 5.0 eq) and 4-(dimethylamino)pyridine (392 mg, 3.21 mmol, 1.0 eq). After 20 minutes stirring at room temperature, solvent is removed and the crude product is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 10:1, v/v) to afford 6-methoxy-2H-1-thia-9-aza-phenanthrene-3-carboxylic acid ethyl ester as a yellow solid (330 mg, 34% yield).

Workup

  1. customsolvent is removed
  2. customthe crude product is purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-d5796fa192514900be2572fa21cbcf09
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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