4-Toluenesulfonyl chloride → HCID 57447104, compound

HRID 2366715Notes

Reaction equation

HRID 2366715 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH2:23])=[O:22])[C:5]2[C:14]3[N:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:36].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[NH2:36][C:7]1[C:6]2[N:15]=[C:3]([CH2:1][CH3:2])[N:4]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH2:23])=[O:22])[C:5]=2[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506716HCID 69506716, compound

Product 1

HCID 57447104HCID 57447104, compound

Procedure

A modification of the method described in Part F of Example 53 was used to treat 6-(2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide (1.18 g, 3.8 mmol) with mCPBA (2.54 g of 70-77% purity) followed by ammonium hydroxide (4 mL), and p-toluenesulfonyl chloride (0.72 g). After the amination reaction was stirred for 15 minutes, a precipitate was present and was isolated by filtration. The precipitate was purified by chromatography using a HORIZON HFPC system (silica cartridge, eluting with 0-55% CMA in chloroform) and dried for three days at 90° C. to provide 0.34 g of 6-(4-amino-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)hexanamide as a light yellow solid, mp 220-221° C.

Workup

  1. customAfter the amination reaction
  2. customwas isolated by filtration
  3. customThe precipitate was purified by chromatography
  4. washa HORIZON HFPC system (silica cartridge, eluting with 0-55% CMA in chloroform)
  5. customdried for three days at 90° C.

Sources & evidence

ORD record
ord-b3ef0d6105a848918a14796db5af334b
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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