Dichloromethane → HCID 90101825, compound

HRID 1485662Notes

Reaction equation

HRID 1485662 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][CH2:36][CH2:37][Br:38])=[C:30]([Cl:39])[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(Cl)Cl.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>CCOC(C)=O>[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[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][CH2:36][CH2:37][Br:38])=[C:30]([Cl:39])[CH:29]=3)[N:23]=[C:22]([O:40][CH2:41][C:42]([F:43])([F:44])[F:45])[N:21]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 90341266HCID 90341266, compound

Product 1

HCID 90101825HCID 90101825, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round-bottom flask equipped with a stir bar and charged with tert-butyl(3-(4-((4-((4-(3-bromopropoxy)-3-chlorobenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)-2,2-dimethylpropyl)carbamate (1.655 g, 2.136 mmol) was added CH2Cl2 (5 mL), and then trifluoroacetic acid (2.50 mL, 32.4 mmol). The solution was stirred at room temperature for 2 h. The solution was transferred to a 250 mL separatory funnel and was diluted with EtOAc (75 mL). The solution was washed with sat. aq. NaHCO3 (75 mL). The aq. phase was extracted with EtOAc (2×75 mL). The combined organics were washed with sat. aq. NaCl (50 mL); dried over MgSO4; filtered; then concentrated in vacuo to afford N-(3-amino-2,2-dimethylpropyl)-4-((4-((4-(3-bromopropoxy)-3-chlorobenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamide trifluoroacetic acid as a colorless solid (1.52 g, 100%). MS m/z=674.25 (M+1)+.

Workup

  1. customTo a 100 mL round-bottom flask equipped with a stir bar
  2. customThe solution was transferred to a 250 mL separatory funnel
  3. washThe solution was washed with sat. aq. NaHCO3 (75 mL)
  4. extractionThe aq. phase was extracted with EtOAc (2×75 mL)
  5. washThe combined organics were washed with sat. aq. NaCl (50 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-3a9cf24f8b1241eb8cf0f82d86111b25
Source dataset
uspto-grants-2016_08
Patent number
US09422311B2

Reaction notes

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