Methanol → HCID 59410242, compound

HRID 2382692Notes

Reaction equation

HRID 2382692 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][OH:12])[C:5]([S:13]([N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3[CH:23]=[CH:24][CH:25]=[CH:26][C:17]2=3)(=[O:15])=[O:14])=[CH:4][C:3]=1[C:27]1[C:28]([CH3:35])=[CH:29][C:30]([C:33]#[N:34])=[N:31][CH:32]=1.C(#N)C.[OH2:39].CO>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:27]2[CH:32]=[N:31][C:30]([C:33]#[N:34])=[CH:29][C:28]=2[CH3:35])=[CH:4][C:5]([S:13]([N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3[CH:23]=[CH:24][CH:25]=[CH:26][C:17]2=3)(=[O:15])=[O:14])=[C:6]([CH:7]=1)[O:8][CH2:9][CH2:10][C:11]([OH:39])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6342AcetonitrileHCID 59410233HCID 59410233, compound

Product 1

HCID 59410242HCID 59410242, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-[2-chloro-4-(3-hydroxy-propoxy)-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-4-methyl-pyridine-2-carbonitrile 8-1 (31 mg, 0.06 mmol) in a mixture of DCM (0.3 mL), acetonitrile (0.3 mL) and water (0.4 mL) was added NaIO4 (38 mg, 0.18 mmol) and RuCl3 (2.5 mg, 0.012 mmol). The mixture was stirred at rt for 40 minutes, then 1 mL of methanol was added. The mixture was filtered and purified by prep. LCMS to afford 3-[5-chloro-4-(6-cyano-4-methyl-pyridin-3-yl)-2-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenoxy]-propionic acid 10-1. MS: 526.0 (M+H)+; tR=4.65 min (method 4). NMR (CDCl3), δ, 8.378 (1H, s), 7.649 (1H, s), 7.621 (1H, s), 7.259 (1H, s), 7.136-7.203 (2H, m), 6.981-7.038 (1H, m), 6.746 (1H, d, J=7.8 Hz), 4.423 (2H, t), 3.728 (2H, m), 2.803-2.842 (4H, m), 2.162 (3H, s), 1.894-1.929 (2H, m), 1.658 (2H, m).

Workup

  1. filtrationThe mixture was filtered
  2. custompurified by prep

Sources & evidence

ORD record
ord-d48d013a533c481a8a77aab5723472e5
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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