2-Amino-5-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-4-trifluoromethyl-benzoic acid methyl ester → HCID 59164515, compound

HRID 906532Notes

Reaction equation

HRID 906532 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:7]([C:20]([F:23])([F:22])[F:21])=[CH:6][C:5]=1[NH2:24]>[Pd].C1COCC1>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][O:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:7]([C:20]([F:21])([F:23])[F:22])=[CH:6][C:5]=1[NH2:24]

Participants

4

Reactant 1

HCID 591644212-Amino-5-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 59164515HCID 59164515, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-amino-5-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-4-trifluoromethyl-benzoic acid methyl ester (2.20 g, 6.16 mmol) and palladium on carbon (250 mg, 10%) in THF (15 mL) was stirred at r.t. for 30 min under hydrogen (5 bars). The mixture was then filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel 60, hexanes/EtOAc 5:1) to afford 2-amino-5-[3-(tetrahydro-pyran-2-yloxy)-propyl]-4-trifluoromethyl-benzoic acid methyl ester (1.99 g, 5.51 mmol, 89%) as a colorless oil, ESI-MS: m/z 384 [M+Na]+, rt 6.20 min)

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by flash chromatography (silica gel 60, hexanes/EtOAc 5:1)

Sources & evidence

ORD record
ord-96cc5edf4cca49da91e6f9c32b446896
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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