Trifluoroacetic acid → (10R,14S)-14-Amino-10-methyl-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-9-one

HRID 1481292Notes

Reaction equation

HRID 1481292 reaction equation
[CH3:1][C@@H:2]1[CH2:19][CH2:18][CH2:17][C@H:16]([NH:20]C(=O)OC(C)(C)C)[C:15]2[CH:28]=[C:11]([CH:12]=[CH:13][N:14]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][C:3]1=[O:29].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:20][C@@H:16]1[C:15]2[CH:28]=[C:11]([CH:12]=[CH:13][N:14]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][C:3](=[O:29])[C@H:2]([CH3:1])[CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736623tert-Butyl N-[(10R,14S)-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-14-yl]carbamate

Product 1

HCID 118236075(10R,14S)-14-Amino-10-methyl-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1(19),2(7),3,5,15,17-hexaen-9-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 45G (950 mg, 2.402 mmol) in DCM (20.300 ml) was added TFA (5.55 ml, 72.1 mmol) dropwise over 10 min. The dark brownish solution was stirred at rt for 1 hour. The reaction mixture was concentrated to give example 45H compound as a dark brownish gum. Used in next step without purification. MS (ESI) m/z: 296.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give example 45H compound as a dark brownish gum
  3. customUsed in next step without purification

Sources & evidence

ORD record
ord-637c001e9c8647d3ae99a6e5750f2166
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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