4-Toluenesulfonyl chloride → HCID 57447075, compound

HRID 2366697Notes

Reaction equation

HRID 2366697 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])[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+:41].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[O:22])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:41])[C:8]=2[N:17]=1)[CH3:2]

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447074HCID 57447074, compound

Product 1

HCID 57447075HCID 57447075, compound

Procedure

The method described in Part F of Example 37 was used to treat 2-(ethoxymethyl)-1-(4-morpholin-4-yl-4-oxobutyl)-1H-imidazo[4,5-c][1,5]naphthyridine (1.42 g, 3.70 mmol) with mCPBA (0.958 g, 5.55 mmol), ammonium hydroxide (4 mL), and p-toluenesulfonyl chloride (0.776 g, 4.07 mmol). Following the chromatographic purification, the resulting solid was dried for 48 hours under high vacuum at 120° C. to provide 0.614 g of 2-(ethoxymethyl)-1-(4-morpholin-4-yl-4-oxobutyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a tan powder, mp 156-157° C.

Workup

  1. customthe chromatographic purification
  2. customthe resulting solid was dried for 48 hours under high vacuum at 120° C.

Sources & evidence

ORD record
ord-6cbf5a8f5d434d3a8f36006f17b8c23e
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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