Triethylamine → Methanesulfonic acid 3-(1-methanesulfonyl-5-methyl-1H-pyrazol-3-ylamino)-6-methoxy-isoquinolin-1-ylmethyl ester

HRID 2101113Notes

Reaction equation

HRID 2101113 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([CH2:18][OH:19])=[N:13][C:12]([NH:20][C:21]1[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=1)=[CH:11]2.CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([N:23]1[C:24]([CH3:26])=[CH:25][C:21]([NH:20][C:12]2[N:13]=[C:14]([CH2:18][O:19][S:2]([CH3:1])(=[O:4])=[O:3])[C:15]3[C:10]([CH:11]=2)=[CH:9][C:8]([O:7][CH3:6])=[CH:17][CH:16]=3)=[N:22]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57799698HCID 57799698, compound

Product 1

HCID 57799576Methanesulfonic acid 3-(1-methanesulfonyl-5-methyl-1H-pyrazol-3-ylamino)-6-methoxy-isoquinolin-1-ylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

MsCl (1.0 g) in 20 mL CH2Cl2 was added slowly to a mixture of [6-Methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-1-yl]-methanol (11.0 g) and Et3N (1.42 g) in 50 mL CH2Cl2 at 0° C. The reaction mixture was stirred at r.t. for 3 h, and then washed with saturated NaHCO3 (aq) and NaCl(aq). The organic layer was dried over Na2SO4, and concentrated to give the crude product.

Workup

  1. washwashed with saturated NaHCO3 (aq) and NaCl(aq)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-879a91b33dde42d1b94d7b91c70a2d33
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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