Chloroform → HCID 178454003, compound

HRID 2239853Notes

Reaction equation

HRID 2239853 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[N:13]([CH:32]=[CH:33][N:34]=3)[N:14]=[C:15]([NH:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]3)[CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.CCOC1C=CC(N)=CC=1.C(Cl)(Cl)Cl.[Cl-].[NH4+]>[Zn].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[C:12]3[N:13]([CH:32]=[CH:33][N:34]=3)[N:14]=[C:15]([NH:17][C@H:18]3[CH2:19][CH2:20][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:28])[CH3:29])[CH2:22][CH2:23]3)[CH:16]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 90764-EthoxyanilineHCID 25517Ammonium ChlorideHCID 178454006HCID 178454006, compound

Product 1

HCID 178454003HCID 178454003, compoundYield 120.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

In a 50 ml round bottom flask was added tert-butyl(trans)-4-(8-(4-nitrophenylamino)imidazo[1,2-b]pyridazin-6-ylamino)cyclohexylcarbamate (0.090 g, 0.19 mmol) from 1c, chloroform (2.0 ml), methanol (2.0 ml), ammonium chloride (0.12 g, 0.19 mmol) and zinc dust (0.13 g, 0.19 mmol). The reaction was allowed to stir for 30 min at room temperature. The reaction was then filtered through a plug of celite and rinsed with dichloromethane to afford 0.1 g of crude tert-butyl(trans)-4-(8-(4-aminophenylamino)imidazo[1,2-b]pyridazin-6-ylamino)cyclohexylcarbamate.

Workup

  1. filtrationThe reaction was then filtered through a plug of celite
  2. washrinsed with dichloromethane

Sources & evidence

ORD record
ord-6827023933d449ac8888d16799f51fa4
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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