Trifluoroacetic acid → HCID 73213800, compound

HRID 1398356Notes

Reaction equation

HRID 1398356 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][N:14]=1)[C:11](=[O:15])[N:10]([CH3:16])[C:9]1[CH:17]=[C:18]([O:21][CH2:22][C@@H:23]([NH:28]C(=O)OC(C)(C)C)[CH2:24][CH:25]([CH3:27])[CH3:26])[CH:19]=[CH:20][C:8]2=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:28][C@@H:23]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:8]2[C:7]3[C:12](=[CH:13][N:14]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=3)[C:11](=[O:15])[N:10]([CH3:16])[C:9]=2[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86710350HCID 86710350, compound

Product 1

HCID 73213800HCID 73213800, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-tert-butyl (1-((2-acetamido-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (140 mg, 0.059 mmol) in CH2Cl2 (15 mL) at 0° C. was added TFA (1.2 mL, 15.58 mmol) and the reaction mixture was stirred at RT for 40 min. After the completion of reaction, the volatile organics were evaporated under reduced pressure and the residue was purified by preparative HPLC (0.1% TFA in water/Acetonitrile) to yield (S)—N-(8-((2-amino-4-methylpentyl)oxy)-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-2-yl)acetamide (2 mg, 3.93 μmol, 6.6% yield) as a mono TFA salt. LC/MS (ESI) m/e 383.2 [(M+H)+, calcd for C21H22N4O3 383.2]; LC/MS retention time (method C): tR=1.80 min; HPLC retention time (method A): tR=5.14 min; HPLC retention time (method B): tR=5.62 min; 1H NMR (400 MHz, CD3OD) δ 9.28 (s, 1H), 8.93 (s, 1H), 8.35 (d, J=8.80 Hz, 1H), 7.17 (s, 1H), 7.15 (d, J=2.00 Hz, 1H), 4.46 (d, J=8.80 Hz, 1H), 4.28 (dd, J=6.40, 10.80 Hz, 1H), 3.76-3.79 (m, 4H), 2.29 (s, 3H), 1.65-1.88 (m, 3H), 1.08 (d, J=4.40 Hz, 3H), 1.07 (d, J=4.40 Hz, 3H).

Workup

  1. customAfter the completion of reaction
  2. customthe volatile organics were evaporated under reduced pressure
  3. customthe residue was purified by preparative HPLC (0.1% TFA in water/Acetonitrile)

Sources & evidence

ORD record
ord-5459be30fbb046fc8b07f1946582e8b3
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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