Methanesulfonyl chloride → HCID 21906516, compound

HRID 988649Notes

Reaction equation

HRID 988649 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)=[O:8].C(N(C(C)C)CC)(C)C.[CH3:41][S:42]([Cl:45])(=[O:44])=[O:43]>C(Cl)Cl>[ClH:16].[ClH:45].[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:17]=[C:2]([NH:1][S:42]([CH3:41])(=[O:44])=[O:43])[CH:3]=[CH:4][C:5]=2[NH:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]3[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=3)[CH2:24][CH2:25]2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21906507HCID 21906507, compound

Product 1

HCID 21906516HCID 21906516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-N-(5-chloropyridin-2-yl)-2-[1-(4-pyridinyl)piperidin-4-ylmethylamino]benzamide (90 mg, 0.21 mmol)and diisopropyl ethylamine (0.036 mL) in methylene chloride (2 mL) was treated with methanesulfonyl chloride (0.016 mL, 0.21 mmol). After 0.25 h, the mixture was concentrated and the residue partitioned between EtOAc and water. The aqueous layer was treated with 1 N NaOH and the resulting solid collected by filtration. The material was further purified by RPHPLC yielding the title compound as a hydrochloride salt.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue partitioned between EtOAc and water
  3. additionThe aqueous layer was treated with 1 N NaOH
  4. filtrationthe resulting solid collected by filtration
  5. customThe material was further purified by RPHPLC

Sources & evidence

ORD record
ord-0733b8a7a5914cc788ad5261ff10b1b8
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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