Trifluoroacetic acid → N-(3-amino-2,2-dimethylpropyl)-6-(6-(4-(3-bromopropoxy)benzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamide

HRID 1485657Notes

Reaction equation

HRID 1485657 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([CH3:47])([CH3:46])[CH2:10][NH:11][C:12](=[O:45])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[CH:25]=[C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][Br:38])=[CH:30][CH:29]=3)[N:23]=[C:22]([O:39][CH2:40][C:41]([F:44])([F:43])[F:42])[N:21]=2)=[N:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]([CH3:47])([CH3:46])[CH2:10][NH:11][C:12](=[O:45])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[CH:25]=[C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][Br:38])=[CH:30][CH:29]=3)[N:23]=[C:22]([O:39][CH2:40][C:41]([F:44])([F:43])[F:42])[N:21]=2)=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679320Tert-butyl 3-(6-(6-(4-(3-bromopropoxy)benzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamido)-2,2-dimethylpropylcarbamate

Product 1

HCID 86679321N-(3-amino-2,2-dimethylpropyl)-6-(6-(4-(3-bromopropoxy)benzylamino)-2-(2,2,2-trifluoroethoxy)pyrimidin-4-ylamino)nicotinamideYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl(3-(6-((6-((4-(3-bromopropoxyl)benzyl)amino)-2-(2,2,2-trifluoroethoxyl)pyrimidin-4-yl)amino)nicotinamido)-2,2-dimethylpropyl)carbamate (10 mg) in DCM (3 mL) was added TFA (0.3 ml). The mixture was stirred at room temperature for 3 hours. All the solvents were removed under vacuum to give N-(3-amino-2,2-dimethylpropyl)-6-(6-(4-(3-bromopropoxyl)benzylamino)-2-(2,2,2-trifluoroethoxyl)pyrimidin-4-ylamino)nicotinamide (8 mg).

Workup

  1. customAll the solvents were removed under vacuum

Sources & evidence

ORD record
ord-d3a4f6de365f42c295b256fa7718f1f6
Source dataset
uspto-grants-2016_08
Patent number
US09422311B2

Reaction notes

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