Phosphorus oxychloride → HCID 86683277, compound

HRID 1852270Notes

Reaction equation

HRID 1852270 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](O)=[N:8][CH:7]=[C:6]2[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22].P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[C:6]([N:14]2[CH2:19][CH2:18][N:17]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:16][CH2:15]2)=[CH:7][N:8]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31297Methanesulfonyl chlorideHCID 178487754HCID 178487754, compound

Product 1

HCID 86683277HCID 86683277, compoundYield 19.72%

Conditions

Temperature
110 °C

Procedure

6-methoxy-4-(piperazin-1-yl)isoquinolin-1-ol (0.15 g, 0.578 mmol) was taken in methane sulfonyl chloride (0.090 mL, 1.157 mmol) and added phosphorous oxychloride (5 mL) and stirred for 1 h at 110° C. The volatiles were evaporated and the crude was poured into ice. This solution PH was adjusted to 9.0 and extracted with ethyl acetate and washed with brine solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude sample was purified by silica gel chromatography using 45% ethyl acetate in pet ether to get 1-chloro-6-methoxy-4-(4-(methylsulfonyl)piperazin-1-yl)isoquinoline (0.041 g, 0.114 mmol, 19.72% yield) as solid. 1H NMR (300 MHz, DMSO-d6): ppm 8.18 (d, J=9.16 Hz, 1H) 7.98 (s, 1H) 7.42-7.50 (m, 1H) 7.38 (s, 1H), 3.99 (s, 3H), 3.41 (br. s., 4H) 3.19 (br. s., 4H) 3.00 (s, 3H). MS: MS m/z 346.20 (M++1).

Workup

  1. customThe volatiles were evaporated
  2. additionthe crude was poured into ice
  3. extractionextracted with ethyl acetate
  4. washwashed with brine solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude sample was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fc988fba85914370a1844bf6885a4c48
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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