Acetylene → HCID 178512852, compound

HRID 1694563Notes

Reaction equation

HRID 1694563 reaction equation
C#C.[NH:3]([CH2:7][CH2:8][CH2:9][CH:10]([NH:14][C:15]([C:17]1[S:18][CH:19]=[CH:20][C:21]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[C:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH:27]=1)(=[O:25])=[O:24])=[O:16])[C:11]([OH:13])=[O:12])[C:4]([NH2:6])=[NH:5].[H][H]>O1CCCC1.O.[Pd]>[NH:3]([CH2:7][CH2:8][CH2:9][C@H:10]([NH:14][C:15]([C:17]1[S:18][CH:19]=[CH:20][C:21]=1[NH:22][S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][CH2:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)[CH:27]=1)(=[O:25])=[O:24])=[O:16])[C:11]([OH:13])=[O:12])[C:4]([NH2:6])=[NH:5]

Participants

6

Reactant 3

HCID 6326AcetyleneHCID 178418361HCID 178418361, compound2×HCID 178512952HCID 178512952, compound

Product 1

HCID 178512852HCID 178512852, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

The acetylene (EG00298/5-Guanidino-2-{[3-(3-pyridin-3-ylethynyl-benzenesulfonyl amino)-thiophene-2-carbonyl]-amino}-pentanoic acid; approx 10 mg) was dissolved in tetrahydrofuran:water (4:1, 2 mL), palladium on charcoal (approx 10% weight) was added and a hydrogen atmosphere introduced by balloon. The reaction mixture was stirred at 20° C. for 24 hours with occasional refilling of the hydrogen balloon. After this time the reaction mixture was filtered over Celite™ and the solvent removed in vacuo. The yellow residue was purified using preparative LCMS.

Workup

  1. filtrationAfter this time the reaction mixture was filtered over Celite™
  2. customthe solvent removed in vacuo
  3. customThe yellow residue was purified

Sources & evidence

ORD record
ord-068569b246a54b20b6ee8ef6704275d2
Source dataset
uspto-grants-2012_04
Patent number
US08158789B2

Reaction notes

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