Ammonia → HCID 58375185, compound

HRID 536641Notes

Reaction equation

FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[S:16]1[C:20]2[CH:21]=[C:22]([C:25]([N:27]3[CH2:34][CH2:33][C:32]4([CH3:36])[CH2:35][CH:28]3[CH2:29][C:30]3[CH:40]=[CH:39][C:38](O)=[CH:37][C:31]=34)=[O:26])[CH:23]=[CH:24][C:19]=2[N:18]=[CH:17]1.C(N(CC)CC)C.N>CN(C)C1C=CN=CC=1.ClCCl>[S:16]1[C:20]2[CH:21]=[C:22]([C:25]([N:27]3[CH2:34][CH2:33][C:32]4([CH3:36])[CH2:35][CH:28]3[CH2:29][C:30]3[CH:40]=[CH:39][C:38]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[CH:37][C:31]=34)=[O:26])[CH:23]=[CH:24][C:19]=2[N:18]=[CH:17]1

Participants

Conditions

Temperature: -10 °C

Procedure

Trifluoromethanesulfonic anhydride (0.77 mL) is added to a solution of benzothiazol-6-yl-(8-hydroxy-6-methyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl)-methanone (1.24 g; for synthesis see Example 92), triethylamine (3.4 mL), and 4-dimethylaminopyridine (10 mg) in dichloromethane (12 mL) chilled to −10° C. under argon atmosphere. The solution is stirred at ca. −5° C. for 30 min and then at room temperature overnight. The reaction solution is added to ice-cold water and then concentrated aqueous ammonia solution is added. The resulting mixture is extracted with dichloromethane, the combined organic extracts are washed with water and dried (MgSO4). The solvent is removed under reduced pressure to give the crude product that is used without further purification.

Workup

customat room temperature
customovernight
additionThe reaction solution is added to ice-cold water
extractionThe resulting mixture is extracted with dichloromethane
washthe combined organic extracts are washed with water
dry with materialdried (MgSO4)
customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-f8ed1bbcf23c4b06b2a9544156e6e801
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859580B2

Reaction notes

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