Sodium hydride → HCID 66753905, compound

HRID 1896336Notes

Reaction equation

HRID 1896336 reaction equation
[Cl-].[CH3:2][C:3]1[S:32][C:6]2=[N:7][C:8]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:9][C:10](=[O:11])[N:5]2[C:4]=1[CH3:33].[H-].[Na+].[CH:36]1([CH2:39][O:40][C:41]2[C:48]([O:49][CH3:50])=[CH:47][CH:46]=[CH:45][C:42]=2[CH:43]=O)[CH2:38][CH2:37]1>CS(C)=O>[CH:36]1([CH2:39][O:40][C:41]2[C:48]([O:49][CH3:50])=[CH:47][CH:46]=[CH:45][C:42]=2/[CH:43]=[CH:12]/[C:8]2[N:7]=[C:6]3[S:32][C:3]([CH3:2])=[C:4]([CH3:33])[N:5]3[C:10](=[O:11])[CH:9]=2)[CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 87135491HCID 87135491, compound

Product 1

HCID 66753905HCID 66753905, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred suspension of Step 2 intermediate (1.0 g, 2.00 mmol) in dry DMSO (12 ml) was treated with NaH (89 mg, 2.240 mmol) and 2-(cyclopropylmethoxy)-3-methoxybenzaldehyde (462 mg, 2.240 mmol) according to the procedure described in Step 3, Intermediate 2 to yield a crude solid which was purified by column chromatography using 2% ethyl acetate in DCM to afford 600 mg of the desired compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 0.32-0.35 (m, 2H), 0.54-0.58 (m, 2H), 1.15-1.21 (m, 1H), 2.26 (s, 3H), 2.59 (s, 3H), 3.73-3.75 (m, 2H), 3.79 (s, 3H), 6.13 (s, 1H), 6.99-7.00 (m, 3H), 7.29-7.31 (m, 1H), 8.03 (d, J=16.2 Hz, 1H).

Workup

  1. customto yield a crude solid which
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-dd74018a4fdc489791ea3ff37e9e3e2f
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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