1-Hydroxybenzotriazole → 5-Bromoisoquinolin-4-carboxylic amide

HRID 1470484Notes

Reaction equation

HRID 1470484 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([OH:14])=O)=[CH:5][N:6]=[CH:7]2.CC[N:17](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([NH2:17])=[O:14])=[CH:5][N:6]=[CH:7]2

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 682819235-Bromoisoquinoline-4-carboxylic acid

Product 1

HCID 682818895-Bromoisoquinolin-4-carboxylic amideYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-bromoisoquinoline-4-carboxylic acid (Intermediate-17) (1 equiv, 2.0 mmol) in dry THF (10.0 ml) were added, DIPEA (3 equiv), HOBT (1.5 equiv), EDC.HCl (1.5 equiv) at RT and the mixture was stirred for 10 min. To this, corresponding amine (1.2 equiv) was added and the reaction mixture was stirred overnight. After completion (TLC), it was concentrated under reduced pressure and the crude product was purified by flash column chromatography to furnish the corresponding amide derivative (60-80%).

Workup

  1. concentrationAfter completion (TLC), it was concentrated under reduced pressure
  2. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-d7796424a0f54b34821a4182919c440e
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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