Hydrochloric Acid → HCID 54544852, compound

Participants

Reaction Steps

(4-Benzyloxy-phenyl)-(6-(5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-furan-2-yl)-quinazolin-4-yl)-amine (0.680 g, 1.30 mmol) was dissolved in THF (10 ml) and 2N aqueous HCl (10 ml) was added. The mixture was stirred at room temperature for 2 hours. The THF was removed in vacuo and the residue diluted with water to preciptate the intermediate (partial hydrolysis) 5-(4-(4-benzyloxy-phenylamino)-quinazolin-6-yl)-furan-2-carboxylic acid (3-methyloxetan-3-yl)-methyl ester which was collected by filtration and washed with water and acetone; δH [2H6]DMSO 12.10 (1H, s), 9.50 (1H, s), 8.87 (1H, s), 8.43 (1H, s), 8.00 (1H, s), 7.66 (2H, d), 7.58 (1H, d), 7.30-7.54 (6H, m), 7.13 (2H, d), 5.16 (2H, s), 4.14 (2H, s), 3.28-3.41 (4H, m), 0.88 (3H, s). This solid was suspended in a mixture of MeOH (15 ml) and NaOH (2N, 15 ml), and the mixture was stirred at room temperature for 2 hours. The reaction was diluted with water to give the title product as a yellow solid, which was collected by filtration (0.375 g, 0.831 mmol, 64%); δH [2H6]DMSO 10.06 (1H, s), 8.91 (1H, s), 8.48 (1H, s), 8.21 (1H, d), 7.80 (1H, d), 7.63 (2H, d), 7.25-7.52 (7H, m), 7.05 (2H, d), 5.10 (2H, s), 3.85 (3H, s); m/z (M+1+) 452.

Provenance & Evidence