4-Methoxypiperidine → HCID 25211191, compound

HRID 572282Notes

Reaction equation

HRID 572282 reaction equation
[CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[CH3:19][O:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>>[CH3:19][O:20][CH:21]1[CH2:26][CH2:25][N:24]([C:16]([C:14]2[S:15][C:11]([C:3]3[C:2]([CH3:1])=[C:6]([C:7]([F:8])([F:9])[F:10])[O:5][N:4]=3)=[CH:12][CH:13]=2)=[O:18])[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 776664-MethoxypiperidineHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Product 1

HCID 25211191HCID 25211191, compoundYield 81%

Procedure

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 4-methoxypiperidine by the method described in Example 2 Method B. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a 1 N aqueous hydrochloric acid solution followed by water. The solid was air dried to afford product as a colorless solid (151 mg, 81%). 1H NMR (CDCl3) 1.64-1.72 (m, 2H), 1.86-1.93 (m, 2H), 2.33 (d, J=1.3, 3H), 3.36 (s, 3H), 3.47-3.58 (m, 3H), 3.87-3.95 (m, 2H), 7.29 (d, J=3.5, 1H), 7.42 (d, J=4.0, 1H). 13C NMR 7.9, 30.9, 42 (br), 56.1, 75.2, 114.7, 118.7 (q, J=271), 128.0, 129.1, 131.1, 140.3, 155.2 (q, J=40), 158.0, 162.7. 19F NMR −63.2. LC/MS 6.31 min, [M+1]+ 375.

Workup

  1. customThe reaction mixture was evaporated to a solid
  2. customtriturated
  3. filtrationfiltered with the aid of water
  4. washwashed with a 1 N aqueous hydrochloric acid solution
  5. customdried

Sources & evidence

ORD record
ord-e3e68e3e9c52418e91095d2f86afdc64
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

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