Trifluoroacetic acid → HCID 90101737, compound

HRID 1485653Notes

Reaction equation

HRID 1485653 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([CH3:48])([CH3:47])[CH2:10][NH:11][C:12](=[O:46])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[N:25]=[C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]([CH2:38][Cl:39])=[CH2:37])=[CH:30][CH:29]=3)[N:23]=[C:22]([O:40][CH2:41][C:42]([F:45])([F:44])[F:43])[N:21]=2)=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]([CH3:48])([CH3:47])[CH2:10][NH:11][C:12](=[O:46])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[N:25]=[C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]([CH2:38][Cl:39])=[CH2:37])=[CH:30][CH:29]=3)[N:23]=[C:22]([O:40][CH2:41][C:42]([F:45])([F:44])[F:43])[N:21]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90101928HCID 90101928, compound

Product 1

HCID 90101737HCID 90101737, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl(3-(4-((4-((4-((2-(chloromethyl)allyl)oxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)-2,2-dimethylpropyl)carbamate (1 g) in DCM (10 mL) was added TFA (3 mL). The mixture was stirred at room temperature for 3 hours. All the solvents were removed under vacuum. The residue was diluted with EtOAc (200 mL), washed with 10% of NaHCO3 (50 mL), brine (50 mL), dried over MgSO4 and concentrated to give N-(3-amino-2,2-dimethylpropyl)-4-(4-(4-(2-(chloromethyl)allyloxy)benzylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzamide (0.8 g).

Workup

  1. customAll the solvents were removed under vacuum
  2. additionThe residue was diluted with EtOAc (200 mL)
  3. washwashed with 10% of NaHCO3 (50 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b629e8349e6496db32b9bd30db8e4bc
Source dataset
uspto-grants-2016_08
Patent number
US09422311B2

Reaction notes

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