Diisopropylethylamine → HCID 58449366, compound

HRID 2278751Notes

Reaction equation

HRID 2278751 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([OH:7])=O.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:35][C:36]1[N:41]=[CH:40][C:39]([CH2:42][NH2:43])=[CH:38][CH:37]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([I:11])[CH:10]=1)[C:5]([NH:43][CH2:42][C:39]1[CH:40]=[N:41][C:36]([CH3:35])=[CH:37][CH:38]=1)=[O:7]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 51825203-Bromo-5-iodobenzoic acidHCID 12214337(6-Methylpyridin-3-yl)methanamine

Product 1

HCID 58449366HCID 58449366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-bromo-5-iodo-benzoic acid (1.4 g, 4.4 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.7 g, 8.8 mmol), 1-hydroxybenzotriazole hydrate (0.20 g, 1.3 mmol), and CH2Cl2 (50 mL) were added (6-methylpyridin-3-yl)methanamine (0.65 g, 5.3 mmol) and N,N-diisopropylethylamine (1.5 mL, 8.8 mmol). The reaction mixture was stirred at room temperature overnight and then concentrated in vacuo. The precipitated solid was washed with water and ethyl ether and dried to afford the product as a white solid. LC-MS: 432.7 [M+l].

Workup

  1. concentrationconcentrated in vacuo
  2. washThe precipitated solid was washed with water and ethyl ether
  3. customdried

Sources & evidence

ORD record
ord-2e39b4270a9a4fa8adcf56860d877a0d
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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