Trifluoroacetic acid → (R)-N-(3-amino-1-(3-fluoro-4-(trifluoromethyl)phenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

HRID 2279537Notes

Reaction equation

HRID 2279537 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:12]([NH:23][C:24]([N:26]2[CH2:35][CH2:34][C:33]3[CH:32]=[N:31][C:30]([NH:36][CH:37]([CH3:39])[CH3:38])=[N:29][C:28]=3[CH2:27]2)=[O:25])[CH2:13][CH2:14][NH:15]C(=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][CH2:14][CH2:13][C@@H:12]([NH:23][C:24]([N:26]1[CH2:35][CH2:34][C:33]2[CH:32]=[N:31][C:30]([NH:36][CH:37]([CH3:39])[CH3:38])=[N:29][C:28]=2[CH2:27]1)=[O:25])[C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:10])([F:9])[F:11])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68294477(R)-tert-butyl 3-(3-fluoro-4-(trifluoromethyl)phenyl)-3-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propylcarbamate

Product 1

HCID 60198657(R)-N-(3-amino-1-(3-fluoro-4-(trifluoromethyl)phenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution 292 (0.090 g, 0.16 mmol) and DCM (3 mL) at RT was added TFA (1 mL) and the reaction was stirred at RT for 1 h and then concentrated to dryness. The resulting product was next dissolved in minimal DCM (using MeOH to aid solubility) and added to a stirring solution of 1M HCl in ether. The resulting solid was filtered, washed with ether and dried to afford 0.060 g (75%) of I-72: MS m/z (APCI-pos) M+1=455.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting product was next dissolved in minimal DCM (using MeOH to aid solubility)
  3. additionadded to a stirring solution of 1M HCl in ether
  4. filtrationThe resulting solid was filtered
  5. washwashed with ether
  6. customdried
  7. customto afford 0.060 g (75%) of I-72

Sources & evidence

ORD record
ord-fc6100b03d6545acaa70112e9f878331
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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