4-Toluenesulfonyl chloride → HCID 57447100, compound

HRID 2366714Notes

Reaction equation

HRID 2366714 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[C:6]2[C:15]3[N:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:37].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[NH2:37][C:8]1[C:7]2[N:16]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[C:6]=2[C:15]2[N:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506701HCID 69506701, compound

Product 1

HCID 57447100HCID 57447100, compound

Procedure

A modification of the method described in Part F of Example 53 was used to treat 6-(2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide (1.20 g, 3.7 mmol) with mCPBA (2.47 g of 70-77% purity) followed by ammonium hydroxide (4 mL), and p-toluenesulfonyl chloride (0.70 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 ground up and dried for three days at 70° C. and then overnight at 95° C. to provide 0.46 g of 6-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide as a white solid, mp 216.5-217.5° C.

Workup

  1. customAfter the amination reaction
  2. customwas isolated by filtration
  3. washwashed with chloroform and water
  4. customdried for three days at 70° C.

Sources & evidence

ORD record
ord-0e0d5818bc32471b9d3448ab829bc062
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

Loading…