Ammonium Chloride → HCID 86687586, compound

HRID 1473529Notes

Reaction equation

HRID 1473529 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:39](Cl)(=[O:41])=[O:40])=[C:34]([O:37][CH3:38])[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:39]([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:40])=[O:41])=[C:34]([O:37][CH3:38])[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 86687587HCID 86687587, compound

Product 1

HCID 86687586HCID 86687586, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask containing ice cold suspension of N-(4-methoxybenzyl)thiazol-2-amine (171 mg, 0.776 mmol) in THF (2844 μl) was added lithium bis(trimethylsilyl)amide (1M in THF) (1479 μl, 1.479 mmol) faster than drop wise. The mixture was stirred for 15 mins prior to the drop wise addition of a solution of 4-chloro-6-methoxyquinoline-7-sulfonyl chloride (216 mg, 0.739 mmol) in THF (2.0 ml, 0.4 ml wash). The solution was allowed to stir for 4 hr (ice melt) providing a brown solution containing primarily product according to LC-MS. The mixture was added to a flask containing sat. aq. NH4Cl. 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 40 g HP silicycle column ramping EtOAc in heptane (0-50%, 10% DCM throughout) affording product, 4-chloro-6-methoxy-N-(4-methoxybenzyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (128 mg, 0.269 mmol, 36.4% yield) as a yellow solid. m/z (ESI) 476.1 (M+H)+.

Workup

  1. additionTo a flask containing
  2. stirringto stir for 4 hr (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 40 g HP silicycle column

Sources & evidence

ORD record
ord-8e006a02b01d4cb3993cb4f745e3b233
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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