Hydrochloric Acid → HCID 131729822, compound

HRID 572295Notes

Reaction equation

HRID 572295 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].C([N:26]1[CH2:31][CH2:30][NH:29][C@H:28]([CH3:32])[CH2:27]1)(OC(C)(C)C)=O.[ClH:33]>O1CCOCC1>[ClH:33].[CH3:32][C@@H:28]1[CH2:27][NH:26][CH2:31][CH2:30][N:29]1[C:16]([C:14]1[S:15][C:11]([C:3]2[C:2]([CH3:1])=[C:6]([C:7]([F:8])([F:9])[F:10])[O:5][N:4]=2)=[CH:12][CH:13]=1)=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Product 1

HCID 131729822HCID 131729822, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 4-N-Boc-2-(R)-methyl-piperazine 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 intermediate N-Boc protected product as a colorless solid (106 mg, 92%). The Boc-protected intermediate was dissolved in a 4 N solution of hydrogen chloride in 1,4,-dioxane (2 mL) and stirred for 2 hr, after which time the reaction mixture was evaporated to approximately ¼ volume and diluted with ethyl ether (4 mL). The resulting solids were filtered and air dried to afford product as a colorless solid (85 mg, 86% overall). 1H NMR (D2O) 1.27 (d, J=7.5, 3H), 2.02 (s, 3H), 3.04 (dt, J=12.7, 3.1, 1H), 3.12-3.18 (m, 2H), 3.30-3.50m (m, 2H), 4.21 (d, J=14.5, 1H), 7.23 (s, 2H). 19F NMR −64.1. LC/MS 4.50 min, [M+1]+ 360.

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
  6. customto afford intermediate N-Boc protected product as a colorless solid (106 mg, 92%)
  7. customafter which time the reaction mixture was evaporated to approximately ¼ volume
  8. additiondiluted with ethyl ether (4 mL)
  9. filtrationThe resulting solids were filtered
  10. customair dried

Sources & evidence

ORD record
ord-3eb1d061b80c4d0aafbe95e9e208948d
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

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