1-Naphthaldehyde → HCID 178455232, compound

HRID 1397602Notes

Reaction equation

HRID 1397602 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Si:13]([O:20][C@@H:21]1[C@H:25]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][C@@H:23]([O:35][C:36]2[CH:41]=[CH:40][N:39]=[C:38]([NH2:42])[C:37]=2[NH2:43])[CH2:22]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[Si:13]([O:20][C@@H:21]1[C@H:25]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][C@@H:23]([O:35][C:36]2[CH:41]=[CH:40][N:39]=[C:38]3[NH:42][C:11]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)=[N:43][C:37]=23)[CH2:22]1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 656671Sodium PyrosulfiteHCID 667979604-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]oxy}pyridine-2,3-diamine

Product 1

HCID 178455232HCID 178455232, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-naphthalenecarboxaldehyde (115 mg, 0.000738 mol), 4-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclo pentyl]oxy}pyridine-2,3-diamine (115.1 mg, 0.0002460 mol) and sodium metabisulfite (0.140 g, 0.000738 mol) in acetonitrile (2.00 mL) was subject to microwave irradiation at 180° C. for 25 mins. The mixture was filtered and the filtrate was concentrated. The residue was purified by preparative plate chromatography (25% EtOAc/hexanes) to afford the title compound (0.101 g, 68%) as a white solid.

Workup

  1. customirradiation at 180° C. for 25 mins
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by preparative plate chromatography (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9103b0f3300d4f5c88c70181fa3f254a
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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