Ammonium Chloride → HCID 86687581, compound

HRID 1473525Notes

Reaction equation

HRID 1473525 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][C:9]2[S:10][CH:11]=[CH:12][N:13]=2)=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([S:38](Cl)(=[O:40])=[O:39])=[C:34]([CH3:37])[CH:35]=2)[N:30]=[CH:29][CH:28]=1.[NH4+].[Cl-]>C1COCC1>[Cl:26][C:27]1[C:36]2[C:31](=[CH:32][C:33]([S:38]([N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:15][CH:14]=3)[C:9]3[S:10][CH:11]=[CH:12][N:13]=3)(=[O:39])=[O:40])=[C:34]([CH3:37])[CH:35]=2)[N:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 578640N-[(4-methoxyphenyl)methyl]-1,3-thiazol-2-amineHCID 2733832Lithium HexamethyldisilazideHCID 86687582HCID 86687582, compound

Product 1

HCID 86687581HCID 86687581, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask containing ice cold suspension of N-(4-methoxybenzyl)thiazol-2-amine (147 mg, 0.665 mmol) in THF (2437 μl) was added lithium bis(trimethylsilyl)amide (1M in THF) (1267 μl, 1.267 mmol) faster than drop wise. The mixture was stirred for 15 min prior to the drop wise addition of a solution of 4-chloro-6-methylquinoline-7-sulfonyl chloride (175 mg, 0.634 mmol) in THF (2.0 ml, 0.5 ml wash). The solution was allowed to stir for 20 min (ice melt) providing a brown solution containing primarily product. The mixture was added to a flask containing sat. aq. NH4Cl and ice. The aqueous mixture was extracted 2× with EtOAc and the combined organics were dried with Na2SO4, filtered, and dried under reduced pressure. The crude material was purified with a 25 g HP Silicycle column ramping EtOAc in heptane (0-50%, 10% DCM throughout) to afford product, 4-chloro-N-(4-methoxybenzyl)-6-methyl-N-(thiazol-2-yl)quinoline-7-sulfonamide (162 mg, 0.352 mmol, 55.6% yield) as a yellow solid with about 15% impurity by LC-MS. m/z (ESI) 460.3 (M+H)+.

Workup

  1. additionTo a flask containing
  2. stirringto stir for 20 min (ice melt)
  3. customproviding a brown solution
  4. additioncontaining primarily product
  5. additionThe mixture was added to a flask
  6. extractionThe aqueous mixture was extracted 2× with EtOAc
  7. dry with materialthe combined organics were dried with Na2SO4
  8. filtrationfiltered
  9. customdried under reduced pressure
  10. customThe crude material was purified with a 25 g HP Silicycle column

Sources & evidence

ORD record
ord-a51323e4a0064c31a3e268e515080d62
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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