Triethylamine → HCID 178430904, compound

HRID 1061525Notes

Reaction equation

CC[N:3]([CH2:6]C)CC.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:9].[CH3:27][C:28]1[CH:29]=[N:30][NH:31][C:32]=1[C:33]1[C:34](C(O)=O)=[CH:35][C:36]2[C:41]([CH:42]=1)=[CH:40][CH:39]=[CH:38][CH:37]=2>C1C=CC=CC=1>[CH3:27][C:28]1[C:32]2[N:31]([C:6](=[O:9])[N:3]=[C:34]3[C:33]=2[CH:42]=[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]2=[CH:35]3)[NH:30][CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Et3N (300 μL, 2.152 mmol) and (PhO)2PON3 (440 μL, 2.064 mmol) were added to a C6H6 (10.0 mL) suspension of 3-(4-methylpyrazol-5-yl)-2-naphthoic acid (Preparation 10) (257 mg, 1.019 mmol), and the mixture was heated at 50° C. for 2 hr. The volatile component was removed in vacuo, and the resulting yellow solid was dissolved in o-dichlorobenzene (8.0 mL) and heated at 150° C. for 4 hr. During the latter heating, there was a gradual evolution of gas accompanied by the formation of a suspension. The reaction mixture was allowed to cool to RT, and the precipitate was filtered and washed with copious ether to afford the title compound as a fluffy light-yellow solid (170.8 mg, 67%). 1H NMR (DMSO, δ=2.50): 11.86 (s, 1H), 8.57 (s, 1H), 8.13 (d, J=8.2, 1H), 7.99 (s, 1H), 7.92 (d, J=8.3, 1H), 7.22 (s, 1H), 7.56 (app t, J=7.21, 1H), 7.49 (app t, J=7.48, 1H), 2.60 (s, 3H). (ESI) m/z (M+H)+=250.00.

Workup

customThe volatile component was removed in vacuo
dissolutionthe resulting yellow solid was dissolved in o-dichlorobenzene (8.0 mL)
temperatureheated at 150° C. for 4 hr
temperatureto cool to RT
filtrationthe precipitate was filtered
washwashed with copious ether

Sources & evidence

ORD record: ord-f51beaf9d6cd49dfa1927f81061537df
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960585B2

Reaction notes

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