HCID 66826179, compound → HCID 68790218, compound

HRID 61657Notes

Reaction equation

HRID 61657 reaction equation
[CH3:1][N:2]([CH3:44])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[N:12]=[C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=1)[N:10]=[C:9]2[NH:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[N:32]=[CH:31]2.[H][H]>CO.[Pd]>[NH2:24][C:20]1[CH:19]=[C:18]([C:11]2[N:10]=[C:9]([NH:27][C:28]3[CH:29]=[C:30]4[C:34](=[CH:35][CH:36]=3)[N:33]([C:37]([O:39][C:40]([CH3:42])([CH3:43])[CH3:41])=[O:38])[N:32]=[CH:31]4)[C:8]3[C:13](=[CH:14][C:15]([O:16][CH3:17])=[C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:44])[CH:7]=3)[N:12]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 66826179HCID 66826179, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68790218HCID 68790218, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of tert-butyl 5-(6-(2-(dimethylamino)ethoxy)-7-methoxy-2-(3-nitrophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.085 g, 0.142 mmol) and 10% Pd/C (0.100 g) in MeOH (20 ml) was hydrogenated at RT using a balloon filled with hydrogen gas. The reaction was heated at 55° C. for 1 h. The reaction mixture filtered through Celite® washing with MeOH. The filtrate was concentrated in vacuo to give tert-butyl 5-(2-(3-aminophenyl)-6-(2-(dimethylamino)ethoxy)-7-methoxyquinazolin-4-ylamino)-1H-indazole-1-carboxylate. (0.065 g, 0.128 mmol, 90%). HPLC retention time 3.42 mins.

Workup

  1. customwas hydrogenated at RT
  2. filtrationThe reaction mixture filtered through Celite®
  3. washwashing with MeOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c9346e5e603f426b8f7a4cdb46d375bd
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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