Sodium hydride → HCID 66753308, compound

HRID 1642397Notes

Reaction equation

HRID 1642397 reaction equation
[Cl-].[CH3:2][C:3]1[N:7]2[C:8](=[O:32])[CH:9]=[C:10]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=[C:6]2[S:5][CH:4]=1.[H-].[Na+].[CH:35]1([CH2:38][O:39][C:40]2[C:47]([O:48][CH3:49])=[CH:46][CH:45]=[CH:44][C:41]=2[CH:42]=O)[CH2:37][CH2:36]1.C1(COC2C(OC)=CC=CC=2/C=C/C2N=C3SC=CN3C(=O)C=2I)CC1>CS(C)=O>[CH:35]1([CH2:38][O:39][C:40]2[C:47]([O:48][CH3:49])=[CH:46][CH:45]=[CH:44][C:41]=2/[CH:42]=[CH:12]/[C:10]2[N:11]=[C:6]3[S:5][CH:4]=[C:3]([CH3:2])[N:7]3[C:8](=[O:32])[CH:9]=2)[CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66753592HCID 66753592, compoundHCID 87135769HCID 87135769, compound

Product 1

HCID 66753308HCID 66753308, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred suspension of Step 2 intermediate (1.0 g, 2.096 mmol) in dry DMSO (12 ml) was treated with NaH (92 mg, 2.306 mmol) and 2-(cyclopropylmethoxy)-3-methoxybenzaldehyde (475 mg, 2.306 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 260 mg of the desired compound as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.31-0.32 (m, 2H), 0.53-0.55 (m, 2H), 1.18-1.22 (m, 1H), 2.66 (s, 3H), 3.73-3.76 (m, 2H), 3.79 (s, 3H), 6.15 (s, 1H), 6.97-7.13 (m, 4H), 7.30-7.33 (m, 1H), 8.07 (d, J=16.2 Hz 1H); ESI-MS (m/z) 369.26 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-e2d0f98cdd3948c8895dcdc955236171
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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