4-Toluenesulfonyl chloride → HCID 58970363, compound

HRID 2366717Notes

Reaction equation

HRID 2366717 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:38].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[NH2:38][C:9]1[C:8]2[N:17]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24])[C:7]=2[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447108HCID 57447108, compound

Product 1

HCID 58970363HCID 58970363, compound

Procedure

A modification of the methods described in Part F of Example 53 was used to treat 6-[2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide (1.70 g, 5.0 mmol) with mCPBA (3.34 g of 70-77% purity) followed by ammonium hydroxide (5.5 mL), and p-toluenesulfonyl chloride (0.95 g). After the amination reaction was stirred for one hour, a precipitate was present and was isolated by filtration and washed with chloroform and water. The precipitate was triturated with 2-propanol (7.5 mL/g at 97° C.), and the mixture was filtered hot. The isolated solid was dried overnight under vacuum and then in a vacuum oven for six days at 65° C. The product was then sonicated in 1 M aqueous sodium hydroxide for 15 minutes, isolated by filtration, washed with deionized water, and dried in a vacuum oven for three days at 90° C. to provide 0.32 g of 6-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]hexanamide as a yellow solid, mp 215-217° C.

Workup

  1. customAfter the amination reaction
  2. customwas isolated by filtration
  3. washwashed with chloroform and water
  4. customThe precipitate was triturated with 2-propanol (7.5 mL/g at 97° C.)
  5. filtrationthe mixture was filtered hot
  6. customThe isolated solid was dried overnight under vacuum
  7. waitin a vacuum oven for six days at 65° C
  8. customThe product was then sonicated in 1 M aqueous sodium hydroxide for 15 minutes
  9. customisolated by filtration
  10. washwashed with deionized water
  11. customdried in a vacuum oven for three days at 90° C.

Sources & evidence

ORD record
ord-a3c16a0ce8f3492a8aaff207482d47ca
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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