Trifluoroacetic acid → HCID 86695920, compound

HRID 870928Notes

Reaction equation

HRID 870928 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[CH:7][CH:8]=[C:9]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][CH2:20][C@@H:21]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH:23]([CH3:25])[CH3:24])=[CH:14][C:13]=3[O:12][CH:11]([CH3:34])[C:10]=12)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[NH2:26][C@@H:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:20][O:19][C:15]1[CH:16]=[CH:17][C:18]2[C:9]3[C:10](=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[N:6]=[CH:7][CH:8]=3)[CH:11]([CH3:34])[O:12][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724432HCID 86724432, compound

Product 1

HCID 86695920HCID 86695920, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl ((2S)-1-((4-acetamido-5-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (0.15 g, 0.319 mmol) in dichloromethane (25 mL) at room temperature was added TFA (0.246 mL, 3.19 mmol) and the mixture stirred for 12 h. After completion of reaction, the solvent was removed under reduced pressure to afford N-(8-(((S)-2-amino-4-methylpentyl)oxy)-5-methyl-5H-chromeno[3,4-c]pyridin-4-yl)acetamide (0.18 g, 0.281 mmol, 58% yield) as a brown oil. The product was carried forward into the next step without further purification. LCMS (ESI) m/e 370.2 [(M+H)+, calcd for C21H28N3O3 370.2]; LC/MS retention time (Method C): tR=1.14 min.

Workup

  1. customAfter completion of reaction
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7bd6fd26acd14bd5af80af68df2525f8
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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