Dichloromethane → 2-methoxyacetyl chloride N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-2-(dimethylamino)acetamide

HRID 61539Notes

Reaction equation

HRID 61539 reaction equation
[CH3:1][N:2]([CH3:40])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:13]2[N:22]=[C:21]([NH:23][C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[N:29](C([O:35][C:36](C)(C)C)=O)[N:28]=[CH:27]4)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)=[O:5].[C:41]([OH:47])([C:43](F)(F)F)=O.C(Cl)[Cl:49]>>[NH:29]1[C:30]2[C:26](=[CH:25][C:24]([NH:23][C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=[C:13]([C:9]4[CH:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][N:2]([CH3:1])[CH3:40])[CH:12]=[CH:11][CH:10]=4)[N:22]=3)=[CH:32][CH:31]=2)[CH:27]=[N:28]1.[CH3:36][O:35][CH2:43][C:41]([Cl:49])=[O:47]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59361935tert-butyl 5-(2-(3-(2-(dimethylamino)acetamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 866424032-methoxyacetyl chloride N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-2-(dimethylamino)acetamide

Procedure

To tert-butyl 5-(2-(3-(2-(dimethylamino)acetamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (560 mg, 1.04 mmol) was added a solution of 1:1 TFA:CH2Cl2 (6 mL) and stirred at RT for 2 h. The reaction mixture was concentrated in vacuo and the residue was triturated with ethyl ether and drops of CH2Cl2 to afford 2-methoxyacetyl chloride N-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenyl)-2-(dimethylamino)acetamide. (325 mg, 0.74 mmol, 71%)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was triturated with ethyl ether and drops of CH2Cl2

Sources & evidence

ORD record
ord-e8ad9f7d38d043349075ca97c9d5b893
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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