Pyridine → A-837093

HRID 494561Notes

Reaction equation

HRID 494561 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]2[NH:6][C:7]([C:12]3[C:13](=[O:29])[C@:14]([CH3:28])([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:15]4[C:20]([C:21]=3[OH:22])=[CH:19][CH:18]=[CH:17][CH:16]=4)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[OH:22][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@@:14]([CH3:28])([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:13](=[O:29])[C:12]=1[C:7]1[NH:6][C:5]2[CH:30]=[CH:31][C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:3][C:4]=2[S:9](=[O:11])(=[O:10])[N:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 135869463(1R)-3-(7-amino-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1-methyl-1-(3-methylbutyl)naphthalen-2(1H)-one

Product 1

HCID 135436761A-837093Yield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 39-6 (310 g, 0.705 mol) and pyridine (167.6 g, 2.12 mol) in dichloromethane (1645 mL) at 18-20° C. was added methanesulfonyl chloride (121.1 g, 1.06 mol) over 45 minutes. The solution was mixed at RT for 16 h then quenched with 1 M HCl (2000 mL). The layers were separated and the organic layer was concentrated under vacuum. The product was crystallized from ethyl acetate/heptane (1/1, 8 volumes) to give the title compound (236.0 g, 65%).

Workup

  1. additionThe solution was mixed at RT for 16 h
  2. customthen quenched with 1 M HCl (2000 mL)
  3. customThe layers were separated
  4. concentrationthe organic layer was concentrated under vacuum
  5. customThe product was crystallized from ethyl acetate/heptane (1/1, 8 volumes)

Sources & evidence

ORD record
ord-7809ec7a19c447419f8ff0f160359a3b
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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