Sodium ethoxide → HCID 44467314, compound

HRID 1642434Notes

Reaction equation

HRID 1642434 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:21][CH:20]=[CH:19][N:5]2[C:6](=[O:18])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[CH:22]1([CH2:25][O:26][C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][C:28]=2[O:35][CH3:36])[CH2:24][CH2:23]1.[O-]CC.[Na+]>C(O)C>[CH:22]1([CH2:25][O:26][C:27]2[CH:34]=[CH:33][C:30](/[CH:31]=[CH:1]/[C:2]3[N:3]=[C:4]4[S:21][CH:20]=[CH:19][N:5]4[C:6](=[O:18])[C:7]=3[C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=3)=[CH:29][C:28]=2[O:35][CH3:36])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 43560398HCID 43560398, compoundHCID 667528027-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 44467314HCID 44467314, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 5 (400 mg, 1.289 mmol) with 4-cyclopropylmethoxy-3-methoxybenzaldehyde (345 mg, 1.602 mmol) in presence of sodium ethoxide (163 mg, 2.418 mmol) in ethanol (20 ml) according to the procedure described in Example 24 to give 297 mg of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.35 (d, J=4.2 Hz, 2H), 0.64 (d, J=7.8 Hz, 2H), 1.30-1.38 (m, 1H), 3.83 (s, 3H), 3.84 (d, J=8.7 Hz, 2H), 6.70 (d, J=15.6 Hz, 1H), 6.80 (d, J=8.1 Hz, 1H), 6.85-6.92 (m, 1H), 6.94-7.00 (m, 2H), 7.53 (d, J=8.1 Hz, 2H), 7.71 (d, J=7.8 Hz, 2H), 7.84 (d, J=15.0 Hz, 1H), 7.95 (d, J=5.1 Hz, 1H); ESI-MS (m/z) 499.32 (M+H)+.

Sources & evidence

ORD record
ord-c7ab27bd70834134a5045d40135aaddb
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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