Water → HCID 178431642, compound

HRID 1269938Notes

Reaction equation

HRID 1269938 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][C:10]1[C:18]([O:19][C@@H:20]2[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]2)=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2.[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>O1CCCC1.ClCCl>[CH3:9][C:10]1[C:18]([O:19][C@@H:20]2[CH2:25][CH2:24][C@H:23]([NH:26][S:28]([CH3:27])(=[O:30])=[O:29])[CH2:22][CH2:21]2)=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[N:13][NH:14]2

Participants

7

Reactant 4

HCID 962WaterHCID 8471Triethylamine3×HCID 31297Methanesulfonyl chloride2×HCID 178431637HCID 178431637, compound

Product 1

HCID 178431642HCID 178431642, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (49.5 μl, 0.355 mmol) was added at 0° C. to a solution of the cis-4-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine hydrochloride (100 mg, 0.355 mmol) obtained in Example 410 in tetrahydrofuran (4 ml), followed by adding dropwise thereto a solution of methanesulfonyl chloride (28 μl, 0.362 mmol) in dichloromethane (2 ml). After 30 minutes, the resulting mixture was heated to room temperature and triethylamine (0.355 mmol) was further added thereto. After 2 hours, triethylamine (0.355 mmol) and methanesulfonyl chloride (0.355 mmol) were further added thereto. After 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The extract solution was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain cis-N-{4-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}methanesulfonamide (31.7 mg, 28%).

Workup

  1. additionby adding dropwise
  2. waitAfter 2 hours
  3. waitAfter 2 hours
  4. extractionextracted with ethyl acetate
  5. concentrationThe extract solution was concentrated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-24a96cd1e4864a598304b75beb1928fd
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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