Dimethylformamide → HCID 86684834, compound

Reaction equation

[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[C:6]2[CH:7]=[C:8]3[O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][C:9]3=[CH:10][C:11]=2[N:12]=[CH:13][CH:14]=1.CN(C=O)C>[Pd].CO>[NH2:29][C:27]1[CH:26]=[CH:25][C:3]([O:4][C:5]2[C:6]3[CH:7]=[C:8]4[O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][C:9]4=[CH:10][C:11]=3[N:12]=[CH:13][CH:14]=2)=[C:2]([F:1])[CH:28]=1

Participants

Procedure

To a par hydrogenation reaction vessel was 4-(2-Fluoro-4-nitro-phenoxy)-7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalene (0.800 g, 1.6 mmol, 1.0 eq.), DMF (50 ml), EtoAc (50 ml), MeOH (50 ml), TEA (5 ml) and 10% Pd/C (200 mg). The vessel was placed on the par hydrogenator at 35 psi overnight. The Pd was filtered and the solvent removed to give 4-(4-Amino-2-Fluoro-phenoxy)-7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1-aza-cyclododeca[b]naphthalene as an off yellow solid (0.78 g, 99% yield). 1HNMR (400 MHz, DMSO): 8.58 (s, 1H), 7.80 (s, 1H), 7.50 (s, 1H), 7.04 (t, 1H), 6.88 (m, 1H), 6.50 (m, 2H), 5.40 (br s, 2H), 4.35 (s, 4H), 3.87 (d, 4H), 3.62 (s, 4H). LC/MS Calcd for (M+H)+401.4. found 401.5.