Pyridine → HCID 51354595, compound

HRID 2077571Notes

Reaction equation

HRID 2077571 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.ClCCl.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1.N1CCCC1>>[CH3:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[CH:20]=[CH:19][C:11]4[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=4[CH:9]=3)[CH:5]=[CH:6][CH:7]=2)(=[O:40])=[O:39])=[CH:36][CH:37]=1

Participants

6

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 74014-Methoxybenzenesulfonyl chlorideHCID 31268PyrrolidineHCID 51354318HCID 51354318, compound

Product 1

HCID 51354595HCID 51354595, compoundYield 77.2%

Procedure

To a mixture of N-(6-(3-aminophenyl)benzo[d]thiazol-2-yl)acetamide (0.030 g, 0.1 mmol), pyridine (0.03 g, 0.3 mmol) in dichloromethane (2 g, 24 mmol) was added 4-methoxybenzene-1-sulfonyl chloride (0.05 g, 0.2 mmol) at RT. The resultant was stirred for 4 h, and then pyrrolidine (0.02 g, 0.3 mmol) was added. The resulting mixture was concentrated and diluted with DMSO (2 ml) and purified by HPLC (5-95% acetonitrile in water). Collected pure solutions were concentrated and diluted with DCM, washed with aq. Na2CO3 solution. The organic layer was dried over sodium sulfate and concentrated to give a white solid (0.035 g, 73%). MS (ESI pos. ion) Found m/z: 454, (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. additiondiluted with DMSO (2 ml)
  3. custompurified by HPLC (5-95% acetonitrile in water)
  4. customCollected pure solutions
  5. concentrationwere concentrated
  6. additiondiluted with DCM
  7. washwashed with aq. Na2CO3 solution
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1d6a276a3e7f4e98a993d15dc0838e13
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…