Trifluoroacetic acid → HCID 86726575, compound

HRID 870613Notes

Reaction equation

HRID 870613 reaction equation
FC(F)(F)C(O)=O.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[NH:17][C:18]1[N:19]=[CH:20][C:21]2[CH2:27][N:26]([C:28](=[O:39])[CH2:29][CH2:30][NH:31]C(=O)OC(C)(C)C)[CH2:25][CH2:24][C:22]=2[N:23]=1>ClCCl>[NH2:31][CH2:30][CH2:29][C:28]([N:26]1[CH2:25][CH2:24][C:22]2[N:23]=[C:18]([NH:17][CH:9]3[CH2:8][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH2:10]3)[N:19]=[CH:20][C:21]=2[CH2:27]1)=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726577HCID 86726577, compound

Product 1

HCID 86726575HCID 86726575, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (1 mL) to a solution of tert-butyl {3-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-oxopropyl}carbamate (0.19 g; 1.0 equiv; 0.44 mmoles) in dichloromethane (1 mL) and stir for 16 hours. Concentrate the mixture and then partition the residue between dichloromethane and 1N sodium hydroxide. Separate the layers and further extract the aqueous layer with dichloromethane. Wash the combined organic extracts with brine, dry over sodium sulfate, filter, and concentrate to afford the desired 3-amino-1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]propan-1-one (0.145 g; 98%): MS (m/z): 338(M+1).

Workup

  1. concentrationConcentrate the mixture
  2. custompartition the residue between dichloromethane and 1N sodium hydroxide
  3. customSeparate the layers
  4. extractionfurther extract the aqueous layer with dichloromethane
  5. washWash the combined organic extracts with brine
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-8acae53f45a74a879fbfc1bebfec7967
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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