Trifluoroacetic acid → HCID 71726888, compound

HRID 2369546Notes

Reaction equation

HRID 2369546 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:45][CH:46]([CH3:48])[CH3:47])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[C:22]([N:25](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)[CH:23]=3)[CH:18]([CH3:44])[O:17][C:15]=2[CH:16]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:7][C@@H:8]([CH2:45][CH:46]([CH3:48])[CH3:47])[CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]2[C:24]3[C:19](=[CH:20][N:21]=[C:22]([NH2:25])[CH:23]=3)[CH:18]([CH3:44])[O:17][C:15]=2[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724444HCID 86724444, compound

Product 1

HCID 71726888HCID 71726888, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl((2S)-1-((2-(bis(4-methoxybenzyl)amino)-5-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)-4-methylpentan-2-yl)carbamate (110 mg, 0.165 mmol) in dichloromethane (10 mL) was added TFA (0.254 mL, 3.29 mmol) and the reaction was stirred at room temperature overnight. The volatiles were evaporated and the crude material was purified by preparative HPLC (0.1% TFA in MeOH) to afford 8-(((S)-2-amino-4-methylpentyl)oxy)-5-methyl-5H-chromeno[3,4-c]pyridin-2-amine (25 mg, 0.069 mmol, 42% yield) as a yellow solid. 1H NMR (400 MHz, MeOD) δ 7.74 (m, 2 H), 6.84 (s, 1 H), 6.75 (dd, J=2.4 Hz, J=8.4 Hz, 1 H), 6.63 (d, J=2.4 Hz, 1 H), 5.18 (m, 1 H), 4.32 (m, 1 H), 4.15 (m, 1 H), 3.65 (m, 1 H), 1.83 (m, 1 H), 1.65 (m, 5 H), 1.04 (m, 6 H); LCMS (ESI) m/e 328.2 [(M+H)+, calcd for C19H26N3O2 328.2]; LC/MS retention time (Method D): tR=1.24 min; HPLC retention time (method A): tR=8.42 min.

Workup

  1. customThe volatiles were evaporated
  2. customthe crude material was purified by preparative HPLC (0.1% TFA in MeOH)

Sources & evidence

ORD record
ord-6b1b8963cd2541c8a2c30fd1007a280f
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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