Trifluoroacetic acid → HCID 71726518, compound

HRID 870921Notes

Reaction equation

HRID 870921 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][CH2:11][C:10]=12)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[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)[CH2:11][O:12][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724428HCID 86724428, compound

Product 1

HCID 71726518HCID 71726518, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-tert-butyl (1-((4-acetamido-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (150 mg, 0.329 mmol) in CH2Cl2 (10 mL) at room temperature was added TFA (0.025 mL, 0.329 mmol) and the solution was stirred at room temperature for 3 h. The solution was concentrated under reduced pressure and the sample was purified by preparative HPLC (0.1% TFA in water and methanol) yielding (S)—N-(8-((2-amino-4-methylpentyl)oxy)-5H-chromeno[3,4-c]pyridin-4-yl)acetamide (40 mg, 0.113 mmol, 33% yield for three steps) as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 8.34 (d, J=5.3 Hz, 1H), 7.81 (d, J=8.7 Hz, 1H), 7.58 (d, J=5.4 Hz, 1H), 6.77 (m, 1H), 6.63 (d, J=2.4 Hz, 1H), 4.94 (s, 2H), 4.03 (m, 1H), 3.85 (m, 1H), 3.33 (m, 1H), 2.21 (s, 3H), 1.81 (m, 1H), 1.43 (m, 2H), 0.99 (m, 6H); LCMS (ESI) m/e 356.2 [(M+H)+, calcd for C20H26N3O3 356.2]; LC/MS retention time (Method C): tR=1.26 min; HPLC retention time (method A): tR=8.02 min; HPLC retention time (method B): tR=9.08 min.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe sample was purified by preparative HPLC (0.1% TFA in water and methanol)

Sources & evidence

ORD record
ord-38dee561aa04411b8f46d59c2048feb1
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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