Methanesulfonyl chloride → HCID 86301487, compound

HRID 513947Notes

Reaction equation

HRID 513947 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=1)[CH:11]=2)(=O)=O.ClC1C=C(C=CC=1)COC1C=C2C(C=C(CO)C=[N:39]2)=CC=1.CCN(C(C)C)C(C)C.CS(Cl)(=O)=O>C1COCC1>[Cl:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][O:17][C:12]1[CH:11]=[C:10]2[C:15]([CH:16]=[C:7]([CH2:6][NH2:39])[CH:8]=[N:9]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86301179HCID 86301179, compoundHCID 90416937HCID 90416937, compound

Product 1

HCID 86301487HCID 86301487, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(7-((3-Chlorobenzyl)oxy)quinolin-3-yl)methyl methanesulfonate. To a solution of (7-((3-chlorobenzyl)oxy)quinolin-3-yl)methanol (Example 35, 55 mg, 0.18 mmol) in THF (1.8 mL) was added DIPEA (0.064 mL, 0.37 mmol), followed by methanesulfonyl chloride (0.014 mL, 0.18 mmol). The reaction was stirred at ambient temperature overnight. The crude reaction was loaded directly onto a column, purification (FCC, SiO2, 0-40%, EtOAc/hexanes) afforded the title compound as a white solid (44 mg, 76%). 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J=2.3 Hz, 1H), 8.10 (s, 1H), 7.74 (d, J=9.0 Hz, 1H), 7.48 (d, J=9.4 Hz, 2H), 7.41-7.28 (m, 4H), 5.20 (s, 2H), 4.76 (s, 2H). [M+H]=318.2

Workup

  1. customThe crude reaction
  2. customwas loaded directly onto a column, purification (FCC, SiO2, 0-40%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-17d0e92daea545ed9809c6a74fdffee4
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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