Formaldehyde → HCID 14797399, compound

HRID 982329Notes

Reaction equation

[CH2:1]([N:4]1[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:9]=2[N:8]([CH3:15])[N:7]2[CH:16]=[CH:17][CH:18]=[C:6]2[CH2:5]1)[C:2]#[CH:3].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[CH2:33]=O>Cl[Cu].O1CCOCC1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH:1]([N:4]2[C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:9]=3[N:8]([CH3:15])[N:7]3[CH:16]=[CH:17][CH:18]=[C:6]3[CH2:5]2)[C:2]#[C:3][CH3:33])[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 150 ml of p-dioxane were added 11-(2-propynyl)-10,11-dihydro-5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine (2.3 g), 4-(2-methoxyphenyl)piperazine (2.1 g), paraformaldehyde (2.0 g), and CuCl (0.02 g). After stirring at 80° C. for three hours, the mixture was concentrated to 6.9 g of brown oil, which was eluted on a silica gel column with 5% methanol/DCM via HPLC. The desired fraction was concentrated to 4.3 g of 11-[1-[4-(2-methoxyphenyl)piperazin-1-yl]-2-butynyl]-10,11-dihydro-5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine, as a light brown oil; MS(EI)M+ @ 442 (6.7%), IR(CHCl3)--C≡CH @ 3300 cm-1.

Workup

concentrationthe mixture was concentrated to 6.9 g of brown oil, which
washwas eluted on a silica gel column with 5% methanol/DCM via HPLC
concentrationThe desired fraction was concentrated to 4.3 g of 11-[1-[4-(2-methoxyphenyl)piperazin-1-yl]-2-butynyl]-10,11-dihydro-5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine, as a light brown oil

Sources & evidence

ORD record: ord-2782063c843445abbecd324032c4258a
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04996205

Reaction notes

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