HCID 25064252, compound → HCID 25064256, compound

HRID 1958728Notes

Reaction equation

HRID 1958728 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[S:13][C:12]([C:14]([NH:16][C@@H:17]([CH2:22][N+:23]([CH3:26])([CH3:25])[CH3:24])[CH2:18][C:19]([O-:21])=[O:20])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO>[CH2:8]([C:9]1[S:13][C:12]([C:14]([NH:16][C@@H:17]([CH2:22][N+:23]([CH3:26])([CH3:25])[CH3:24])[CH2:18][C:19]([O-:21])=[O:20])=[O:15])=[CH:11][CH:10]=1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 25064252HCID 25064252, compound

Product 1

HCID 25064256HCID 25064256, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-(5-(phenylethynyl)thiophene-2-carboxamido)-4-(trimethylammonio)-butanoate (15 mg, 0.04 mmol) was dissolved into MeOH (3 mL). The solution was purged with nitrogen and 10% palladium on carbon (5 mg) was added. The vessel was purged with hydrogen and stirred for 1 h. The mixture was filtered through celite and solvents removed in vacuo to give the title compound (13 mg, 88%) as a white solid. 1H NMR (400 MHz, CD3OD) δ 7.51 (d, 1H, J=3.9 Hz), 7.27-7.23 (m, 2H), 7.19-7.14 (m, 3H), 6.81 (d, 1H, J=3.8 Hz), 4.85-4.77 (m, 1H), 3.72-3.58 (m, 2H), 3.22 (s, 9H), 3.16 (t, 2H, J=7.8 Hz), 2.98 (t, 2H, J=7.4 Hz), 2.59-2.48 (m, 2H); MS ESI 375.2 [M+H]+, calcd for [C20H26N2O3S+H]+ 375.2

Workup

  1. customThe solution was purged with nitrogen and 10% palladium on carbon (5 mg)
  2. additionwas added
  3. customThe vessel was purged with hydrogen
  4. filtrationThe mixture was filtered through celite and solvents
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-fd852a8950804a2a8ef4a7eacff85b2d
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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