1-((4-methoxyphenyl)methyl)-1H-pyrazol-5-amine → HCID 59490360, compound

HRID 2383411Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of (E)-6-((dimethylamino)methylene)-2-(methylamino)-7,8-dihydroquinazolin-5(6H)-one (2.8 g, 12 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (2.69 g, 13 mmol) was added trifluoroacetic (1 mL). The reaction mixture was heated at 100° C. for 16 hours. The reaction was then cooled to room temperature followed by addition of isopropanol (20 mL). The reaction mixture was the stirred for 30 minutes and the supernatant decanted. The residue was dried under reduced pressure. The crude product was purified using flash column chromatography (SiO2, gradient from 100 hexanes to 15% EtOAc in hexanes) to give desired product (1.0 g, 22%) as solid. 1H NMR (CDCl3, 400 MHz): δ 9.32 (s, 1H), 7.90 (s, 1H), 7.75 (s, 1H), 7.40 (d, J=8.0 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 5.52-5.48 (m, 1H), 5.62 (s, 2H), 3.76 (s, 3H), 3.18-3.04 (m, 5H), 3.0-2.88 (m, 2H); LCMS [M+H]: 373.

Workup

additionwas added trifluoroacetic (1 mL)
temperatureThe reaction was then cooled to room temperature
customThe residue was dried under reduced pressure
customThe crude product was purified

Sources & evidence

ORD record: ord-d687c29f962a40bdb25a136fdfd14a6f
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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