Triethylamine → HCID 11284284, compound

HRID 1593526Notes

Reaction equation

HRID 1593526 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([N:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=3)[C:10](=[O:19])[C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])[S:8][C:4]=2[CH:3]=1.CCN(CC)CC.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>C(Cl)Cl>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:10]([N:9]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[C:7]1[S:8][C:4]2[CH:3]=[C:2]([NH:1][S:40]([CH3:39])(=[O:42])=[O:41])[CH:31]=[CH:30][C:5]=2[N:6]=1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11155728HCID 11155728, compound

Product 1

HCID 11284284HCID 11284284, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 33.2 mg (0.07 mmol) N-(6-Amino-benzothiazol-2-yl)-2,4-dichloro-N-(3,4-dimethoxy-phenyl)-benzamide in 0.7 ml DCM, 18.2 mg (0.18 mmol) NEt3 and 10.3 mg (0.091 mmol) methanesulfonyl chloride in 0.2 ml DCM was reacted for 16 h at room temperature. After evaporation of all volatiles the residue was taken up in DMF/acetonitrile and subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient to yield 9.6 mg (25%) of the title compound. MS (m/e): 552.1 (MH+, 100%).

Workup

  1. customwas reacted for 16 h at room temperature
  2. customAfter evaporation of all volatiles the residue
  3. customHPLC separation on reversed phase
  4. washeluting with an acetonitrile/water gradient

Sources & evidence

ORD record
ord-90312c80213b45c78d490ed474fa4cc5
Source dataset
uspto-grants-2007_11
Patent number
US07297707B2

Reaction notes

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