4-Bromobenzoic acid → HCID 8763081, compound

HRID 494207Notes

Reaction equation

HRID 494207 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][N:6]=[CH:7]3)=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 114644-Bromobenzoic acidHCID 707665-AminoisoquinolineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 8763081HCID 8763081, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-aminoisoquinoline (800 mg, 5.54 mmol), 4-bromobenzoic acid (1.68 g, 8.3 mmol), (3-dimethylaminopropyl)-ethyl-carbodiimide hydrochloride (1.64 g, 8.3 mmol) and 4-dimethylaminopyridine (70 mg, 0.6 mmol) was stirred at room temperature overnight. The mixture was diluted with DCM, washed with saturated aqueous sodium bicarbonate solution and water, then dried over MgSO4 and concentrated in vacuo to give the crude product. Purification by flash column chromatography eluting with an EtOAc/40-60° C. pet. ether gradient gave the title compound as a white solid (1.48 g). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.29 (br, 2H), 8.57 (d, 1H), 8.11 (d, 1H), 7.97, (d, 2H), 7.90 (d, 2H), 7.66 (m, 3H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product
  5. customPurification by flash column chromatography
  6. washeluting with an EtOAc/40-60° C. pet. ether gradient

Sources & evidence

ORD record
ord-c6bccd27c5cc4ff9b34a822d94f840a6
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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