Trimethylsilyldiazomethane → HCID 22243932, compound

HRID 890981Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]([NH:23][C:24]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:31])=[N:14][CH2:15][CH2:16][CH:17]3[CH2:21][CH2:20][CH2:19][N:18]3[CH3:22])=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:32][CH3:33].[CH3:34][Si](C=[N+]=[N-])(C)C>>[CH3:33][O:32][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[O:1][CH3:34])[N:9]=[CH:8][N:7]=[C:6]2[NH:12][C:13]([NH:23][C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:31])=[N:14][CH2:15][CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][N:18]1[CH3:22]

Participants

Reactant 2

HCID 167693Trimethylsilyldiazomethane

HCID 135697907HCID 135697907, compound

Product 1

HCID 22243932HCID 22243932, compound

Procedure

Using an analogous procedure to that described in Example 11. N-(7-hydroxy-6-methoxyquinazolin-4-yl)-N′-(2,6-dimethylphenyl)-N″-[2-(N-methylpyrrolidin-2-yl)ethyl]guanidine was reacted with trimethylsilyldiazomethane to give the title compound; NMR Spectrum: (DMSOd6, 100° C.) 1.65 (m, 3H), 1.68 (m, 1H), 1.8–1.96 (m, 2H), 2.07 (q, 1H), 2.15 (s, 3H), 2.32 (s, 6H), 2.32 (s, 6H), 2.79 (br t, 1H), 2.59 (m, 1H), 2.69 (m, 1H), 3.84 (s, 3H), 3.95 (s, 3H), 7.08 (s, 1H), 7.20 (m, 4H), 7.74 (s, 1H), 8.47 (s, 1H), 10.9–11.3 (br s, 1H); Mass Spectrum: M+H+ 463.

Sources & evidence

ORD record: ord-7b1c36f282ca46a4afadd344a845a099
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001904B1

Reaction notes

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