Sodium ethoxide → HCID 86636081, compound

HRID 1642451Notes

Reaction equation

HRID 1642451 reaction equation
C[C:2]1[N:3]=[C:4]2[S:22][CH:21]=[CH:20][N:5]2[C:6](=[O:19])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.[CH:23]1([O:28][C:29]2[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1.[O-][CH2:40]C.[Na+]>C(O)C>[CH:23]1([O:28][C:29]2[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:30]=2/[CH:31]=[CH:40]/[C:21]2[S:22][C:4]3=[N:3][CH:2]=[C:7]([C:8]4[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=4)[C:6](=[O:19])[N:5]3[CH:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 6484666HCID 6484666, compoundHCID 66753265HCID 66753265, compound

Product 1

HCID 86636081HCID 86636081, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 15 (350 mg, 1.012 mmol) with 2-cyclopentyloxy-3-methoxybenzaldehyde (330 mg, 1.501 mmol) in presence of sodium ethoxide (146 mg, 2.147 mmol) in ethanol (15 ml) according to the procedure of Example 24 to give 251 mg of the desired product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.54-1.62 (m, 6H), 1.75-1.82 (m, 2H), 3.77 (s, 3H), 4.80-4.87 (m, 1H), 6.84-6.93 (m, 2H), 6.98 (d, J=4.8 Hz, 2H), 7.46-7.52 (m, 5H), 7.98 (d, J=4.2 Hz, 1H), 8.10 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 529.49 (M+H)+.

Sources & evidence

ORD record
ord-7fa00fb4b2424026aa0cac12828bd182
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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