Triethylamine → (R)-(3-methyl-4-(1-phenylpyrido[4,3-d]pyridazin-4-yl)piperazin-1-yl)(piperidin-1-yl)methanone

HRID 1514377Notes

Reaction equation

HRID 1514377 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]=[N:10][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=12.C(N(CC)CC)C.[N:31]1([C:37](Cl)=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH3:1][C@H:2]1[N:3]([C:8]2[C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[C:11]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:10][N:9]=2)[CH2:4][CH2:5][N:6]([C:37]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:38])[CH2:7]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 2420851-Piperidinecarbonyl chlorideHCID 57657605(R)-4-(2-methylpiperazin-1-yl)-1-phenylpyrido[3,4-d]pyridazine

Product 1

HCID 25226951(R)-(3-methyl-4-(1-phenylpyrido[4,3-d]pyridazin-4-yl)piperazin-1-yl)(piperidin-1-yl)methanone

Procedure

Using methods described in Example 18, and starting with (R)-4-(2-methylpiperazin-1-yl)-1-phenylpyrido[4,3-d]pyridazine 16 (125 mg, 409 μmol, triethylamine (80 μl, 614 μmol), and piperidine-1-carbonyl chloride (67 μl, 532 μmol) afforded (R)-(3-methyl-4-(1-phenylpyrido[4,3-d]pyridazin-4-yl)piperazin-1-yl)(piperidin-1-yl)methanone 38. MS 416.2 (calc'd) 417.3 (M+H, found).

Sources & evidence

ORD record
ord-8ceb57d7f8c3404b8fb9740f80c3d4ae
Source dataset
uspto-grants-2012_07
Patent number
US08222251B2

Reaction notes

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