Trifluoroacetic acid → HCID 86724443, compound

HRID 870955Notes

Reaction equation

HRID 870955 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[CH:10]=[C:11]3[C:22]4[CH:21]=[CH:20][C:19](OC[C@@H](NC(=O)OC(C)(C)C)CC(C)C)=[CH:18][C:17]=4[O:16][CH:15]([CH3:38])[C:12]3=[CH:13][N:14]=2)=CC=1.C(O)(C(F)(F)F)=O>ClCCl>[CH3:38][CH:15]1[C:12]2=[CH:13][N:14]=[C:9]([NH2:8])[CH:10]=[C:11]2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86724444HCID 86724444, compound

Product 1

HCID 86724443HCID 86724443, 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 8-4(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, 2H), 6.84 (s, 1H), 6.75 (dd, J=2.4 Hz, J=8.4 Hz, 1H), 6.63 (d, J=2.4 Hz, 1H), 5.18 (m, 1H), 4.32 (m, 1H), 4.15 (m, 1H), 3.65 (m, 1H), 1.83 (m, 1H), 1.65 (m, 5H), 1.04 (m, 6H); 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-87b2caa036d14ae78a4abd2c198aabf3
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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