4-Toluenesulfonyl chloride → HCID 69000171, compound

HRID 81893Notes

Reaction equation

HRID 81893 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[CH3:12][O:13][CH2:14][CH2:15][C:16]1[N:17]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1.[OH-].[NH4+:42].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClC(Cl)C.ClCCl.[Cl-].[Na+].O>[NH2:42][C:20]1[C:19]2[N:28]=[C:16]([CH2:15][CH2:14][O:13][CH3:12])[N:17]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:39])[CH3:38])[C:18]=2[C:27]2[N:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=1

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 68997121HCID 68997121, compound

Product 1

HCID 69000171HCID 69000171, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Chloroperoxybenzoic acid (7.8 g of 77%) was added in a single portion to a solution of tert-butyl N-{4-[2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butyl}carbamate (7 g) in dichloroethane (100 mL). The reaction mixture was stirred at ambient temperature for 3 hours, Concentrated ammonium hydroxide (100 mL) was added and the reaction mixture was stirred until a suspension formed. Para-toluenesulfonyl chloride (3.6 g) was added in a single portion. The reaction mixture was stirred at ambient temperature for 2 hours and then diluted with dichloromethane and brine. The organic layer was separated, washed with brine (×2), dried over magnesium sulfate, filtered through a layer of CELITE filter aid, and then concentrated under reduced pressure to provide 8.83 g of crude tert-butyl N-{4-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]butyl}carbamate as a brown solid.

Workup

  1. stirringthe reaction mixture was stirred until a suspension
  2. customformed
  3. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  4. customThe organic layer was separated
  5. washwashed with brine (×2)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered through a layer of CELITE
  8. filtrationfilter aid
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ca1c1d8146446d5899c52c536e43a8c
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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