3-Iodo-4-methoxyaniline → HCID 58710073, compound

HRID 2375878Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].Cl[C:12]1[N:13]=[CH:14][C:15]2[CH:20]=[C:19]([C:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH:26]=3)[NH:18][C:16]=2[N:17]=1>C(O)CCC>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:14]2[C:15]3[CH:20]=[C:19]([C:21]4[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH:26]=4)[NH:18][C:16]=3[N:17]=[CH:12][N:13]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 95 °C

Procedure

3-Iodo-4-methoxyaniline (0.670 g, 2.0 mmol) was added to a solution of tert-butyl 4-(chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (0.598 g, 2.4 mmol) in n-butanol (10 mL). The mixture was heated to 95° C. for 15 h. The solvent was removed and the residue was purified by silica gel chromatography (5% MeOH in dichloromethane) to afford the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ=1.43 (s, 9H), 2.46 (m, 2H), 3.56 (m, 2H), 3.80 (s, 3H), 4.03 (m, 2H), 6.38 (s, 1H), 6.72 (s, 1H), 7.00 (d, J=9.2 Hz, 1H), 7.85 (dd, J=2.8, 8.8 Hz, 1H), 8.34 (s, 1H), 9.27 (s, 1H), 11.93 (s, 1H). MS (ES+): m/z 547.91 [MH+]. HPLC: tR=3.39 min (ZQ2000, polar—5 min).

Workup

customThe solvent was removed
customthe residue was purified by silica gel chromatography (5% MeOH in dichloromethane)

Sources & evidence

ORD record: ord-ea8cb4ff21354c2bb1db7692c0d41de2
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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