Methanesulfonyl chloride → HCID 21034952, compound

HRID 1833124Notes

Reaction equation

HRID 1833124 reaction equation
[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([C:17]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=2[F:27])=[O:18])=[N:5][CH:4]=1.Cl.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:27][C:20]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:19]=1[C:17]([C:6]1[C:7]2[C:12](=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=2)[C:3]([CH2:2][NH:1][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:4][N:5]=1)=[O:18]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 131725820HCID 131725820, compound

Product 1

HCID 21034952HCID 21034952, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(4-Aminomethyl-6,7-dimethoxy-isoquinolin-1-yl)-(2-fluoro-5-methoxy-phenyl)-methanone (Example 27) (100.5 mg, 0.2269 mmol) was suspended in 5 ml of methylene chloride. The solution was cooled to −78° C. and methanesulfonyl chloride (0.0195 ml, 1.10 eq) was added followed by the addition of N,N-diisopropylethylamine (0.122 ml, 3.0 eq). The mixture was stirred at −78° C. for 1 hr and then at room temperature overnight. The mixture was evaporated and the residue was purified through a flash column chromatography using ethyl acetate and hexane (4/1 ratio) to give N-[1-(2-Fluoro-5-methoxy-benzoyl)-6,7-dimethoxy-isoquinolin-4-ylmethyl]-methanesulfonamide (70 mg, 69%). ES-MS calcd for C21H21N21O6S (m/e) 448.47, obsd 449.0 (M+H).

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was evaporated
  4. customthe residue was purified through a flash column chromatography

Sources & evidence

ORD record
ord-994c22d3aabf4717b243a6fa715da79c
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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