Acetamide → HCID 57585137, compound

HRID 2077585Notes

Reaction equation

HRID 2077585 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19].[CH3:21][S:22](Cl)(=[O:24])=[O:23].N1C=CC=CC=1.C(N)(=O)C>C(Cl)Cl.O.CCN(CC)CC>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH:15][S:22]([CH3:21])(=[O:24])=[O:23])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 178AcetamideHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 57584985HCID 57584985, compound

Product 1

HCID 57585137HCID 57585137, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a slurry of 6-(6-chloro-5-(dimethylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (60 mg, 197 μmol) in DCM (2 mL) was added methanesulfonyl chloride (400 μL, 5168 μmol), and pyridine (300 μL). After overnight, Et3N (0.3 mL) was added. After overnight, the mixture was diluted with H2O and stirred for several days. The mixture was filtered, washed with H2O to give a solid that is mostly the product (Rf 2.20), with small amount of Acetamide (Rf 3.39, m/e 347). The solid was washed with EtOAc, and hot EtOAc containing 5% MeOH to give the product as a brown solid (40 mg, 53%). MS (ESI, POS. ION) M/Z: calc'd for C15H15ClN4O2S2: 382.0. found: 383.0. 1H NMR (400 MHz, DMSO-d6) 5 ppm 2.84 (s, 6H) 3.03 (s, 3H) 7.41 (d, J=6.06 Hz, 1H) 7.66-7.87 (m, 2H) 8.26 (d, J=26.21 Hz, 2H) 12.90-13.23 (m, 1H).

Workup

  1. waitAfter overnight
  2. filtrationThe mixture was filtered
  3. washwashed with H2O
  4. customto give a solid
  5. washThe solid was washed with EtOAc, and hot EtOAc containing 5% MeOH

Sources & evidence

ORD record
ord-1e4ce9eec5a3403f8b6108617668d09d
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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