4-Toluenesulfonyl chloride → HCID 66958588, compound

HRID 1364072Notes

Reaction equation

HRID 1364072 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]3[N:21]4[CH2:22][CH2:23][CH2:24][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][C:20]4=[N:19][C:14]=3[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:46].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[NH2:46][C:15]1[C:14]2[N:19]=[C:20]3[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:24][CH2:23][CH2:22][N:21]3[C:13]=2[C:12]2[C:17](=[CH:18][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[N:16]=1

Participants

5

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 66958691HCID 66958691, compound

Product 1

HCID 66958588HCID 66958588, compound

Procedure

The methods described in Part I of Example 368 were used to treat tert-butyl 3-benzyloxy-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate (5.52 g, 12.4 mmol, Example 369 Parts A through D) with mCPBA (4.17 g of 77% purity, 18.6 mmol) followed by ammonium hydroxide (25 mL) and p-toluenesulfonyl chloride (2.6 g, 13.7 mmol) and purify the final compound to provide 2.07 g of tert-butyl 6-amino-3-benzyloxy-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate.

Workup

  1. custompurify the final compound

Sources & evidence

ORD record
ord-79e54fe6a0a4446192ce90f0c490d0e6
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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