Methanesulfonyl chloride → (5-Chloromethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine

HRID 1170133Notes

Reaction equation

HRID 1170133 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:19]O)[N:10]=2)=[CH:4][CH:3]=1.CS([Cl:25])(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[Cl:25][CH2:19][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[CH:17]=[CH:18][C:9]([NH:8][CH2:7][C:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)=[N:10]2

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 44218152{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol

Product 1

HCID 68436366(5-Chloromethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-methanol (example 41, step A, 70 mg, 0.261 mmol) was dissolved in 2 mL tetrahydrofurane and methanesulfonyl chloride (34 mg, 0.297 mmol) and N,N-diisopropyl ethyl amine (41 mg, 0.318 mmol) were added. The reaction mixture was stirred at room temperature overnight and the solvent was evaporated off. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). (5-Chloromethyl-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine was obtained as a brown solid (59 mg, 79%), MS: m/e=287.0 (M+H+).

Workup

  1. customthe solvent was evaporated off
  2. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

Sources & evidence

ORD record
ord-e2cac7a370c34b74b95a55a09558e1dd
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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