Benzoic acid, 2-chloro-5-(chlorosulfonyl)- → h-NTPDase8-IN-1

HRID 59301Notes

Reaction equation

HRID 59301 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15]1([NH2:18])[CH2:17][CH2:16]1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:13])(=[O:12])[NH:18][CH:15]2[CH2:17][CH2:16]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-HCID 69828Cyclopropylamine

Product 1

HCID 16768315h-NTPDase8-IN-1Yield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-5-(chlorosulfonyl)benzoic acid (4.0 g, 15.68 mmol) in DCM (60 mL) was added cyclopropyl amine (1.8 g, 31.57 mmol) and the reaction mixture was stirred at RT for 16 h. The reaction mass was concentrated and the residue was diluted with ice cold water and acidified with dilute HCl. The crude solid was filtered off, washed with water and dried to afford 3.0 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 0.37 (s, 2H), 0.49 (d, J=5.4 Hz, 2H), 2.12-2.13 (m, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.91 (d, J=8.4 Hz, 1H), 8.13 (s, 1H), 8.18 (s, 1H), 13.92 (br s, 1H).

Workup

  1. concentrationThe reaction mass was concentrated
  2. additionthe residue was diluted with ice cold water
  3. filtrationThe crude solid was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-57f2ee6e028a4bac873e0a391adb8b2d
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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