Diisopropylethylamine → HCID 90729912, compound

HRID 851973Notes

Reaction equation

HRID 851973 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:5][NH:6][CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:14].CCN(C(C)C)C(C)C.[Cl:29][C:30]1[S:34][C:33]([S:35](Cl)(=[O:37])=[O:36])=[CH:32][CH:31]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:5][N:6]([CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:14])[S:35]([C:33]1[S:34][C:30]([Cl:29])=[CH:31][CH:32]=1)(=[O:37])=[O:36]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 607631023-[[(3-Fluoro-4-methoxyphenyl)methyl]amino]hexahydro-2H-azepin-2-one

Product 1

HCID 90729912HCID 90729912, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

rac-3-(3-Fluoro-4-methoxy-benzylamino)-azepan-2-one (213 mg, 0.80 mmol) was dissolved in CH2Cl2 (7.7 ml) and treated with DMAP (30 mg, 0.24 mmol), Hünig's base (0.30 ml, 1.76 mmol) and ⅛ of the cooled (0° C.) reaction mixture was reacted with 5-chloro-thiophene-2-sulfonyl chloride (48 mg, 0.22 mmol) and shaken overnight in a parallel reaction block. Solvent was removed under reduced pressure and the residue dissolved in aqueous acetonitrile solution and purified using high throughput preparative RP(C18) chromatography: lyophilisate 13 mg;

Workup

  1. temperaturecooled
  2. custom(0° C.) reaction mixture
  3. customSolvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in aqueous acetonitrile solution
  5. custompurified

Sources & evidence

ORD record
ord-bc2f9594f6c8475884c5c2b5be92cb62
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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