Potassium Carbonate → 6-[2-(3-Methylpentyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy]nicotinamide

HRID 130881Notes

Reaction equation

[CH2:1]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][NH:2]1.[C:22]([O-])([O-])=O.[K+].[K+].BrC[CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33]>CN(C=O)C>[CH3:34][CH:32]([CH2:31][CH3:30])[CH2:33][CH2:22][N:2]1[CH2:3][CH2:4][CH2:5][C:6]2[CH:11]=[C:10]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)[CH:9]=[CH:8][C:7]=2[CH2:1]1

Participants

Conditions

Temperature: 80 °C

Procedure

Mix 6-(2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yloxy)nicotinamide (Example 447, Part E, 55.6 mg, 0.20 mmol), K2CO3 (54.2 mg, 0.39 mmol), and 1-bromo-4-methylpentane (43 uL, 0.29 mmol) in DMF (1.0 mL). Heat at 80° C. overnight. Remove DMF azeotropically with xylenes. Purify by flash chromatography, eluting with 70:25:5 EtOAc/CH2Cl2/2.0 M NH3 in MeOH to afford the title compound (43.1 mg, 60%): MS ES+ 368.4 (M+H)+, HRMS calcd for C22H30N3O2 368.2338 (M+H)+, found 368.2330, time 0.39 min; Anal. Calcd for C22H29N3O2.0.1CH2Cl20.1MeOH: C, 70.32; H, 7.87; N, 11.08. Found: C, 70.05; H, 7.52; N, 11.01.

Workup

customPurify by flash chromatography
washeluting with 70:25:5 EtOAc/CH2Cl2/2.0 M NH3 in MeOH

Sources & evidence

ORD record: ord-99763678197f44a38f0e357eda6cd6eb
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07381719B2

Reaction notes

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