Sodium ethoxide → 2-{(E)-2-[(2-Cyclopropylmethoxy)-3-methoxyphenyl]-1-ethenyl}-3-(4-trifluoro methyl-phenyl)-4H-benzo[4,5][1,3]thiazolo-[3,2-a]pyrimidin-4-one

HRID 1642460Notes

Reaction equation

HRID 1642460 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[O:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[C:7]1[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=1[S:5]2.[CH:26]1([CH2:29][O:30][C:31]2[C:38]([O:39][CH3:40])=[CH:37][CH:36]=[CH:35][C:32]=2[CH:33]=O)[CH2:28][CH2:27]1.[O-]CC.[Na+]>C(O)C>[CH2:27]1[CH2:28][CH:26]1[CH2:29][O:30][C:31]1[C:38]([O:39][CH3:40])=[CH:37][CH:36]=[CH:35][C:32]=1/[CH:33]=[CH:1]/[C:2]1[N:3]=[C:4]2[S:5][C:6]3[CH:25]=[CH:24][CH:23]=[CH:22][C:7]=3[N:8]2[C:9](=[O:21])[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66753266HCID 66753266, compound

Product 1

HCID 444680822-{(E)-2-[(2-Cyclopropylmethoxy)-3-methoxyphenyl]-1-ethenyl}-3-(4-trifluoro methyl-phenyl)-4H-benzo[4,5][1,3]thiazolo-[3,2-a]pyrimidin-4-oneYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 23 (250 mg, 0.690 mmol) with 2-Cyclopropylmethoxy-3-methoxybenzaldehyde (200 mg, 0.970 mmol) in presence of sodium ethoxide (94 mg, 1.380 mmol) in ethanol (15 ml) according to the procedure outlined in Example 24 to give 160 mg of the desired product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.28-0.30 (m, 2H), 0.51-0.53 (m, 2H), 0.90-1.01 (m, 1H), 3.69 (d, J=7.5 Hz, 2H), 3.77 (s, 3H), 6.92 (d, J=15.6 Hz, 2H), 6.98-7.00 (m, 2H), 7.56-7.64 (m, 4H), 7.84-7.86 (m, 2H), 8.06-8.08 (m, 1H), 8.22 (d, J=15.6 Hz, 1H), 8.84-8.86 (m, 1H); ESI-MS (m/z) 549.36 (M+H)+.

Sources & evidence

ORD record
ord-0e6d7ff8856f4d0a9ba0e18a20fee04b
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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