Dimethylformamide → HCID 66614123, compound

HRID 510104Notes

Reaction equation

[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:23]=[C:22](N)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[N:6]1.N(OCCC(C)C)=O.CN(C)C=O>O1CCCC1>[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[N:6]1

Participants

Conditions

Temperature: 95 °C

Procedure

200 mg (0.540 mmol) of the compound from example 5 were suspended in tetrahydrofuran (2.0 ml), then 145 μl (1.08 mmol) of isopentyl nitrite were added and the reaction mixture was heated to reflux for 30 min. Subsequently, dimethylformamide (1.0 ml) and 145 μl of isopentyl nitrite were added and the mixture was stirred at 95° C. for a further 5 h. The reaction mixture was subsequently separated directly by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient) and the product-containing mixed fractions were concentrated. The crude product was subsequently further purified by means of HPLC (eluent: water/methanol/1% trifluoroacetic acid 28:65:7). This gave 30 mg (15% of theory) of the title compound in solid form.

Workup

temperaturethe reaction mixture was heated
temperatureto reflux for 30 min
customThe reaction mixture was subsequently separated directly by means of preparative HPLC (eluent: acetonitrile-water with 0.1% formic acid gradient)
additionthe product-containing mixed fractions
concentrationwere concentrated
customThe crude product was subsequently further purified by means of HPLC (eluent: water/methanol/1% trifluoroacetic acid 28:65:7)

Sources & evidence

ORD record: ord-e74197476da84161860a29fb199885ca
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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