Sodium Carbonate → (S)-(2-methyl-4-(1-(4-(trifluoromethyl)phenyl)pyrido[3,4-d]pyridazin-4-yl)piperazin-1-yl)(piperidin-1-yl)methanone

HRID 1514368Notes

Reaction equation

HRID 1514368 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[C@@H:10]([CH3:22])[CH2:9]2)=[C:4]2[CH:23]=[N:24][CH:25]=[CH:26][C:3]=12.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][C@H:10]1[CH2:9][N:8]([C:5]2[N:6]=[N:7][C:2]([C:32]3[CH:33]=[CH:34][C:29]([C:28]([F:39])([F:38])[F:27])=[CH:30][CH:31]=3)=[C:3]3[CH:26]=[CH:25][N:24]=[CH:23][C:4]=23)[CH2:13][CH2:12][N:11]1[C:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57657606(S)-(4-(1-chloropyrido[3,4-d]pyridazin-4-yl)-2-methylpiperazin-1-yl)(piperidin-1-yl)methanone

Product 1

HCID 25226396(S)-(2-methyl-4-(1-(4-(trifluoromethyl)phenyl)pyrido[3,4-d]pyridazin-4-yl)piperazin-1-yl)(piperidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Using methods described in Example 1, and starting with (S)-(4-(1-chloropyrido[3,4-d]pyridazin-4-yl)-2-methylpiperazin-1-yl)(piperidin-1-yl)methanone 7 (150 mg, 400 μmol), Pd(PPh3)4 (23 mg, 20 μmol), 4-(trifluoromethyl)phenylboronic acid (106 mg, 560 μmol), and 2 M sodium carbonate (400 μl, 800 μmol), (S)-(2-methyl-4-(1-(4-(trifluoromethyl)phenyl)pyrido[3,4-d]pyridazin-4-yl)piperazin-1-yl)(piperidin-1-yl)methanone 8 was obtained. MS 484.2 (calc'd) 485.2 (M+H, found).

Sources & evidence

ORD record
ord-e06f6e81cb814a68af76a6fe8ba3e90b
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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