Diisopropylethylamine → Ethyl 5-[9-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]pentanoate

HRID 1514243Notes

Reaction equation

[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][NH:24][CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44]>C(#N)C>[C:7]([C:6]1[CH:9]=[C:10]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:28]4[O:27][CH2:26][CH2:25][N:24]([CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)[N:14]=2)[CH:11]=[CH:12][C:5]=1[O:4][CH:2]([CH3:1])[CH3:3])#[N:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[(1-methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1,4-benzoxazepin-9-yl)-1,2,4-oxadiazol-5-yl]benzonitrile (Example 32) (100 mg, 0.204 mmol) in acetonitrile (10 ml) was added N,N-diisopropylethylamine (0.07 ml, 0.408 mmol) and ethyl 5-bromopentanoate (0.06 mL, 0.408 mmol). The reaction mixture was heated to 80° C. overnight then was allowed to cool and the solvent evaporated. Purification of the residue by flash chromatography, eluting with (40-100% ethyl acetate in cyclohexane) gave the title compound as an off white solid (70 mg).

Workup

temperatureto cool
customthe solvent evaporated
customPurification of the residue by flash chromatography
washeluting with (40-100% ethyl acetate in cyclohexane)

Sources & evidence

ORD record: ord-5a0f8ab0f6424a9b8454c01f0a0b8993
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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