Water → HCID 9821385, compound

HRID 843128Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:9]=2[C:10]=1[CH2:11][N:12]=[N+]=[N-])=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:9]=2[C:10]=1[CH2:11][NH2:12])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

3-Azidomethyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-carboxylic acid ethyl ester (49 mg) and triphenylphosphine (50 mg) were dissolved in THF (2.5 ml). To the solution was added water (0.3 ml) and the mixture was heated to 70° C. overnight. The reaction mixture was diluted with ethyl acetate (5 ml) and washed with brine (5 ml), then dried over anhydrous sodium sulfate. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography developed by dichloromethane-methanol giving 3-aminomethyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-carboxylic acid ethyl ester as a colorless oil (15 mg). FAB-MS: m/z 384 (MH+); 1H-NMR (CDCl3): δ 1.45 (3H, t, J=7.3 Hz), 2.12 (2H, quintet, J=6.3 Hz), 2.90 (2H, t, J=6.6 Hz),3.85 (2H, s), 4.24 (2H, t, J=6.3 Hz), 4.31 (2H, s), 4.45 (2H, q, J=7.3 Hz), 6.68 (1H, d, J=8.3 Hz), 7.16 (1H, d, J=8.3 Hz), 7.21 (1H, dd, J=4.9 Hz, 7.9 Hz), 7.35 (1H, t, J=8.3 Hz), 7.68 (1H, d, J=7.9 Hz), 8.48 (1H, dd, J=1.7 Hz, 4.9 Hz), 8.56 (1H, d, J=1.7 Hz).

Workup

washwashed with brine (5 ml)
dry with materialdried over anhydrous sodium sulfate
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-17c0d931699d422bb90de1eabaee106a
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376491B1

Reaction notes

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