Water → HCID 69301471, compound

HRID 902442Notes

Reaction equation

HRID 902442 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[S:12][C:11]([S:13]([NH:16][CH:17]2[CH:23]3[CH2:24][CH2:25][CH:18]2[CH2:19][C:20]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:21]=2[CH2:22]3)(=[O:15])=[O:14])=[CH:10][CH:9]=1.[CH3:32][O:33][CH2:34]Cl.O>C1COCC1>[Cl:7][C:8]1[S:12][C:11]([S:13]([N:16]([CH:17]2[CH:23]3[CH2:24][CH2:25][CH:18]2[CH2:19][C:20]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:21]=2[CH2:22]3)[CH2:32][O:33][CH3:34])(=[O:15])=[O:14])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 23665647Potassium tert-butoxideHCID 59701811HCID 59701811, compound

Product 1

HCID 69301471HCID 69301471, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (1.0M in THF; 1.33 ml, 1.33 mmol) was added to a solution of 5-chloro-N-(2-cyano-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[a][8]annulen-11-yl)thiophene-2-sulfonamide (Example 176) (350 mg, 0.89 mmol) in THF (10 ml) and stirred for 20 mins. Chloromethyl methyl ether (108 μl, 1.42 mmol) was added and the reaction stirred overnight at RT. More reagents were added as necessary until the reaction was complete by NMR. The reaction mixture was poured into water (25 ml) and extracted with ethyl acetate (2×25 ml). The combined organic layers were washed with brine, dried over MgSO4 and evaporated to give 5-chloro-N-(2-cyano-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[a][8]annulen-11-yl)-N-(methoxymethyl)thiophene-2-sulfonamide (388 mg, quant.).

Workup

  1. stirringthe reaction stirred overnight at RT
  2. additionMore reagents were added as necessary until the reaction
  3. extractionextracted with ethyl acetate (2×25 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-6906465d9a854d13bfbf7bcc20b4685e
Source dataset
uspto-grants-2008_04
Patent number
US07365196B2

Reaction notes

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