Dimethylcarbamoyl Chloride → (R)-N,N,3-trimethyl-4-(1-phenylpyrido[4,3-d]pyridazin-4-yl)piperazine-1-carboxamide

HRID 1514378Notes

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.[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34]>>[CH3:31][N:32]([CH3:36])[C:33]([N:6]1[CH2:5][CH2:4][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)[C@H:2]([CH3:1])[CH2:7]1)=[O:34]

Participants

Reactant 3

HCID 6598Dimethylcarbamoyl Chloride

HCID 8471Triethylamine

HCID 57657605(R)-4-(2-methylpiperazin-1-yl)-1-phenylpyrido[3,4-d]pyridazine

Product 1

HCID 25226952(R)-N,N,3-trimethyl-4-(1-phenylpyrido[4,3-d]pyridazin-4-yl)piperazine-1-carboxamide

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 (86 μl, 614 μmol) and N,N-dimethylcarbamoyl chloride (41 μl, 450 μmol) afforded (R)—N,N,3-trimethyl-4-(1-phenylpyrido[4,3-d]pyridazin-4-yl)piperazine-1-carboxamide 39. MS 376.2 (calc'd) 377.2 (M+H, found).

Sources & evidence

ORD record: ord-5fee955763be4fe9ac9d1b930bae91fd
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222251B2

Reaction notes

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