Ethyl Acetate → HCID 59403477, compound

HRID 1514183Notes

Reaction equation

Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]4[CH2:28][NH:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:29]=3)[N:15]=2)=[CH:10][C:7]=1[C:8]#[N:9])[CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].CCOC(C)=O>CN(C=O)C>[C:8]([C:7]1[CH:10]=[C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]4[CH2:28][N:27]([CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:26][CH2:25][CH2:24][C:23]=4[CH:29]=3)[N:15]=2)[CH:12]=[CH:13][C:6]=1[O:5][CH:3]([CH3:2])[CH3:4])#[N:9]

Participants

Conditions

Temperature: 60 °C

Procedure

2-[(1-Methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-2-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride (Example 3) (70 mg, 0.170 mmol) and caesium carbonate (167 mg, 0.511 mmol) in dry DMF (5 ml) were treated with ethyl 4-bromobutyrate (0.037 ml, 0.256 mmol) and stirred at 60° C. for 2 hours. Additional quantities of ethyl 4-bromobutyrate (37 ul) were added and the reaction heated at 60° C. for 3 hours. The reaction was left standing overnight. EtOAc (50 ml) was added and the mixture washed with water (2×60 ml), dried over anhydrous MgSO4 and evaporated to yield the title compound (90 mg) as a clear, colourless oil. MS (ES) C28H32N4O4 requires 488; found 489.0 (M+H)+.

Workup

temperaturethe reaction heated at 60° C. for 3 hours
waitThe reaction was left
waitstanding overnight
washthe mixture washed with water (2×60 ml)
dry with materialdried over anhydrous MgSO4
customevaporated

Sources & evidence

ORD record: ord-089eb08a634d4b37ad417ea5d944f94f
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222245B2

Reaction notes

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