Formic Acid → HCID 86651536, compound

HRID 1809455Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH:15]2[N:11]3[C:12](=[C:16]([C:19]4[CH:26]=[CH:25][C:22]([C:23]#N)=[CH:21][CH:20]=4)[N:17]=[CH:18][C:10]3=[CH:9][CH2:8][C:7]1=[O:27])[CH2:13][CH2:14]2.C(O)=[O:35]>O=[Pt]=O.C1COCC1>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][N:6]1[CH:15]2[N:11]3[C:12](=[C:16]([C:19]4[CH:20]=[CH:21][C:22]([CH:23]=[O:35])=[CH:25][CH:26]=4)[N:17]=[CH:18][C:10]3=[CH:9][CH2:8][C:7]1=[O:27])[CH2:13][CH2:14]2

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of (A5) and PtO2 (0.1 eq.) in a solvent mixture of HCO2H (80% sol. in water)/THF=2.5:1 (0.2 M) was heated to 60° C. for 4 h. After cooling, the catalyst was filtered through a pad of celite, then, the solvent was reduced in vacuo and the residue partioned between sat. aq. NaHCO3 and DCM. The aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave the title compound which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ 9.96 (1H, s), 7.78 (2H, d, J=7.8 Hz), 7.85-7.78 (3H, m), 7.72 (1H, d, J=8.6 Hz), 7.29 (1H, d, J=7.8 Hz), 7.27-7.18 (1H, m), 6.50-6.40 (2H, m), 4.78 (2H, s), 3.79 (3H, s), 3.75 (3H, s), 3.70-3.60 (2H, m), 3.30-3.20 (2H, m). MS (ES+) C26H23N3O4 requires: 441, found: 442 (M+H)+.

Workup

temperatureAfter cooling
filtrationthe catalyst was filtered through a pad of celite
customThe aqueous phase was separated
extractionextracted several times with DCM
washThe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
customEvaporation of the solvent

Sources & evidence

ORD record: ord-14f3481c9afd4bacba58a6ad1d861b63
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362030B2

Reaction notes

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