Dimethylamine → N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-[4-(tetrahydropyran-4-yl)piperazin-1-yl]acetamide

HRID 2238810Notes

Reaction equation

HRID 2238810 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.CNC.C(O)C.Br[CH2:20][C:21]([NH:23][C:24]1[S:25][C:26]([C:34]([CH:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[O:35])=[C:27]([C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)=[O:22]>C1COCC1.C(OCC)C>[O:30]1[CH:31]=[CH:32][CH:33]=[C:29]1[C:27]1[N:28]=[C:24]([NH:23][C:21](=[O:22])[CH2:20][N:10]2[CH2:11][CH2:12][N:7]([CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH2:8][CH2:9]2)[S:25][C:26]=1[C:34]([CH:36]1[CH2:37][CH2:38][O:39][CH2:40][CH2:41]1)=[O:35]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 702EthanolHCID 219423151-(Oxan-4-yl)piperazineHCID 231445052-Bromo-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]acetamide

Product 1

HCID 23144662N-[4-(2-Furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]-2-[4-(tetrahydropyran-4-yl)piperazin-1-yl]acetamideYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that in Example 533, by using 1-(tetrahydropyran-4-yl)piperazine (154 mg, 9.00 mmol) in place of the solution of dimethylamine in THF, followed by reslurrying with a mixed solvent of ethanol and diethyl ether, the entitled Compound 571 (79.8 mg, 54%) was obtained from Compound 531; (120 mg, 0.300 mmol).

Sources & evidence

ORD record
ord-9e67d579d5fc4b6da249dd3c7f5f5806
Source dataset
uspto-grants-2010_05
Patent number
US07718808B2

Reaction notes

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