HCID 69598138, compound → HCID 58746608, compound

HRID 724643Notes

Reaction equation

HRID 724643 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:6]([NH:8][C@@H:9]([C:25]1[NH:29][C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=2[N:26]=1)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH:18]=2)=[CH:13][CH:12]=1)=[O:7])(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([NH:4][C@@H:5]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:6]([NH:8][C@@H:9]([C:25]1[NH:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=1)[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[S:21](=[O:23])(=[O:22])[NH:20][C:19](=[O:24])[CH2:18]2)=[CH:15][CH:16]=1)=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 69598138HCID 69598138, compound

Product 1

HCID 58746608HCID 58746608, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2S)-2-(acetylamino)-N-{(1R)-1-(1H-benzimidazol-2-yl)-2-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl}-3-phenylpropanamide (5.0 mg, 0.009 mmol) in methanol (1.5 mL) was added 5% palladium on carbon (3 mg, 0.03 mmol), and mixed for 1.5 h under hydrogen gas (50 psi). Product was filtered and purified by preparative LCMS to afford the final product (1.9 mg, 38%). 1H NMR (500 MHz, CD3OD): δ 7.73–7.76 (m, 2H), 7.58–7.60 (m, 2H), 7.43 (d, J=7.0 Hz, 2H), 7.23–7.26 (m, 5H), 7.14–7.16 (m, 2H), 5.42–5.47 (m, 1H), 5.11–5.16 (m, 1H), 4.52–4.56 (m, 1H), 3.40–3.46 (m, 2H), 2.76–2.92 (m, 4H), 1.90 (s, 3H); LCMS found for C29H30N5O5S (M+H)+: m/z=560.1

Workup

  1. additionmixed for 1.5 h under hydrogen gas (50 psi)
  2. filtrationProduct was filtered
  3. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-f271de9f7e3a49aa8ca6e7015330260a
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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