Ammonium Chloride → HCID 86687591, compound

HRID 1473534Notes

Reaction equation

HRID 1473534 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](=[C:32]([CH3:41])[C:33]([S:37](Cl)(=[O:39])=[O:38])=[CH:34][CH:35]=2)[N:30]=[CH:29][CH:28]=1.[NH4+].[Cl-]>C1COCC1>[Cl:26][C:27]1[C:36]2[C:31](=[C:32]([CH3:41])[C:33]([S:37]([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:38])=[O:39])=[CH:34][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 86687592HCID 86687592, compound

Product 1

HCID 86687591HCID 86687591, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask containing ice cold suspension of N-(4-methoxybenzyl)thiazol-2-amine (557 mg, 2.53 mmol) in THF (9.0 ml) was added lithium bis(trimethylsilyl)amide (1M in THF) (4816 μl, 4.82 mmol) faster than drop wise. The mixture was stirred for 15 mins prior to the drop wise addition of a solution of 4-chloro-8-methylquinoline-7-sulfonyl chloride (665 mg, 2.408 mmol) in THF (6.0 ml, 1.0 ml wash). The solution was allowed to stir for 20 mins (ice melt) providing a brown solution containing primarily product according to LC-MS. 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) affording product, 4-chloro-N-(4-methoxybenzyl)-8-methyl-N-(thiazol-2-yl)quinoline-7-sulfonamide (326 mg, 0.709 mmol, 29.4% yield) as a yellow solid. m/z (ESI) 460.3 (M+H)+.

Workup

  1. additionTo a flask containing
  2. stirringto stir for 20 mins (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-c23b20fbb0db461782f2456829e3aef3
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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