Trifluoroacetic acid → HCID 71727015, compound

HRID 870973Notes

Reaction equation

HRID 870973 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]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])=[C:14]([O:34][CH3:35])[C:13]=3[O:12][CH2:11][C:8]2=[CH:9][N:10]=1)(=[O:3])[CH3:2].[C:36]([OH:42])([C:38](F)(F)F)=[O:37]>ClCCl.O>[C:36]([O-:42])(=[O:37])[CH3:38].[NH4+:4].[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:7]3[C:8](=[CH:9][N:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=3)[CH2:11][O:12][C:13]=2[C:14]=1[O:34][CH3:35]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724453HCID 86724453, compound

Product 2

HCID 517165Ammonium AcetateHCID 71727015HCID 71727015, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-tert-butyl (1-((2-acetamido-7-methoxy-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (111 mg, 0.088 mmol) in dichloromethane (2 mL) was added TFA (0.027 mL, 0.352 mmol) dropwise and the reaction mixture was stirred at room temperature for 12 h. After completion of reaction, the volatiles were removed under reduced pressure to afford a residue which was purified by prep. HPLC (Sunfire C18 3.5 um, 19×150 mm column and 10 mM ammonium acetate in water) to yield (S)—N-(8-((2-amino-4-methylpentyl)oxy)-7-methoxy-5H-chromeno[3,4-c]pyridin-2-yl)acetamide (10 mg, 0.022 mmol, 25% yield) as white solid. 1H NMR (400 MHz, MeOD) δ 8.38 (s, 1H), 8.17 (s, 1H), 7.6 (d, J=8.8 Hz, 1H), 6.88 (d, J=8.8 Hz, 1H), 5.18 (s, 2H), 3.9 (s, 3H), 2.2 (s, 3H), 1.94 (m, 3H), 1.86-1.81 (m, 1H), 1.70-1.65 (m, 1H), 1.63-1.55 (m, 1H), 1.04 (m, 6H); LCMS (ESI) m/e 386.2 [(M+H)+, calcd for C21H28N3O4 386.2]; LC/MS retention time (Method E): tR=1.99 min; HPLC retention time (method A): tR=8.80 min; HPLC retention time (method B): tR=9.73 min.

Workup

  1. customAfter completion of reaction
  2. customthe volatiles were removed under reduced pressure
  3. customto afford a residue which
  4. customwas purified by prep

Sources & evidence

ORD record
ord-70c8354d75bf4bbbafc8aa0125a1b94e
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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