Ammonia → N-[1-(4-bromophenyl)ethyl]-2-(5-isoquinolinyl)acetamide

HRID 2056857Notes

Reaction equation

HRID 2056857 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([CH2:11][C:12]([O:14]C)=O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.BrC1C=CC(CN)=CC=1.N.Cl>O>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([NH:25][C:12](=[O:14])[CH2:11][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][N:2]=[CH:1]3)[CH3:24])=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 775714-BromobenzylamineHCID 911751-(4-Bromophenyl)ethylamineHCID 22337565Methyl 2-(isoquinolin-5-yl)acetate

Product 1

HCID 22032664N-[1-(4-bromophenyl)ethyl]-2-(5-isoquinolinyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared using the procedure described in Example 132C using the product from Example 133B and 1-(4-bromophenyl)ethanamine instead of the product from Example 132B and 4-bromobenzylamine. 1H NMR (300 MHz, d6-DMSO) 9.81 (s, 1H), 9.00 (d, 1H), 8.70 (d, 1H), 8.48 (d, 1H), 840 (d, 1H), 8.04 (d, 1H), 7.92 (m, 1H), 7.51 (d, 2H), 7.23 (d, 2H), 4.84 (m, 1H), 4.10 (s, 2H), 1.35 (d, 3H). MS (DCI/NH3) m/e 369 (M+H)+; Anal. Calcd. For C19H17N2OBr. 1.0 HCl. 1.0 H2O: C 53.86; H 4.76; N 6.61. Found: C 53.47; H 4.53; N 6.76.

Sources & evidence

ORD record
ord-b517a7df43d242978ea4f5721c539987
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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