Ethyl 4-bromobutyrate → Ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]butanoate

HRID 1514212Notes

Reaction equation

HRID 1514212 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11].CCN(C(C)C)C(C)C.Br[CH2:39][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]>CN(C=O)C>[Cl:2][C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][N:24]([CH2:39][CH2:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:25][CH2:26][C:20]=4[CH:19]=3)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 76300Ethyl 4-bromobutyrateHCID 81531DiisopropylethylamineHCID 684687897-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

Product 1

HCID 59403483Ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]butanoateYield 110.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (Example 17) (65 mg, 0.155 mmol), DIPEA (0.104 ml, 0.593 mmol) and ethyl 4-bromobutanoate (0.048 ml, 0.339 mmol) were stirred at 60° C. in DMF (10 ml) for 24 hours. The reaction mixture was partitioned between EtOAc (˜30 ml) and water (˜30 ml) and the aqueous layer extracted once more with EtOAc (˜40 ml). The combined organics were concentrated in vacuo to yield the crude title compound (100 mg, 0.171 mmol) as an orange solid. MS (ES): C27H3235ClN3O4 requires 497; found 498 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (˜30 ml) and water (˜30 ml)
  2. extractionthe aqueous layer extracted once more with EtOAc (˜40 ml)
  3. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-ec85970a5249426ebd38f244a81ec375
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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