Water → HCID 57410724, compound

HRID 1502307Notes

Reaction equation

HRID 1502307 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH2:18])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([NH:18][S:21]([CH3:20])(=[O:23])=[O:22])[N:14]=[CH:15]3)=[CH:10][CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 574102447-(5-Fluoro-2-methylphenyl)isoquinolin-3-amine

Product 1

HCID 57410724HCID 57410724, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 7-(5-fluoro-2-methylphenyl)isoquinolin-3-amine (150 mg, 0.595 mmol) in pyridine (5 mL) was added methanesulfonyl chloride (137 mg, 1.20 mmol) dropwise at 0° C. The resulting mixture was stirred at room temperature overnight. A small amount of water was added to the reaction mixture, and it was extracted with ethyl acetate. The organic phase was pooled and concentrated. It was purified by prep-HPLC to give the desired product (80.5 mg, 41.0%). LCMS (ESI): RT (Min)=1.181, M+H+=330.9, method=A; 1H NMR (400 MHz, DMSO-d6) δ 10.57 (s, 1H), 9.17 (s, 1H), 8.04 (s, 1H), 7.93 (d, J=8.8 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.44 (s, 1H), 7.38-7.34 (m, 1H), 7.15 (d, J=9.2 Hz, 2H), 3.30 (s, 3H), 2.22 (s, 3H).

Workup

  1. extractionwas extracted with ethyl acetate
  2. concentrationconcentrated
  3. customIt was purified by prep-HPLC

Sources & evidence

ORD record
ord-8c9d3d145b6843529240341e59d029ee
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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