Sodium ethoxide → HCID 86636079, compound

HRID 1642432Notes

Reaction equation

HRID 1642432 reaction equation
C[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.[CH3:22][O:23][C:24]1[C:25]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.[O-][CH2:41]C.[Na+]>C(O)C>[CH3:22][O:23][C:24]1[C:25]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[C:26](/[CH:27]=[CH:41]/[C:20]2[S:21][C:4]3=[N:3][CH:2]=[C:7]([C:8]4[CH:9]=[CH:10][C:11]([C:14]([F:16])([F:15])[F:17])=[CH:12][CH:13]=4)[C:6](=[O:18])[N:5]3[CH:19]=2)[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 16228509HCID 16228509, compoundHCID 667528027-Methyl-6-[4-(trifluoromethyl)phenyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 86636079HCID 86636079, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 5 (350 mg, 1.127 mmol) with 3-methoxy-2-(pyridin-2-ylmethoxy)benzaldehyde (411 mg, 1.692 mmol) in presence of sodium ethoxide (153 mg, 2.207 mmol) in ethanol (20 ml) according to the procedure described in Example 24 to give 289 mg of the desired product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.81 (s, 3H), 5.00 (s, 2H), 6.79 (d, J=16.2 Hz, 1H), 6.90-6.98 (m, 1H), 7.05 (d, J=4.5 Hz, 2H), 7.30-7.36 (m, 1H), 7.46-7.60 (m, 4H), 7.72-7.84 (m, 3H), 7.99-8.04 (m, 1H), 8.10 (d, J=15.6 Hz, 1H), 8.48-8.56 (m, 1H); ESI-MS (m/z) 512.18 (M+H)+.

Sources & evidence

ORD record
ord-59943dc0f36f474c96efa7639ebd95e1
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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