Sodium hydride → HCID 16086950, compound

HRID 1724117Notes

Reaction equation

HRID 1724117 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11](C2C=CC(C(OC)=O)=CC=2)[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18])=[CH:7][CH:6]=1)=[O:4].[C:30]([C:33]1[CH:49]=[CH:48][C:36]([CH2:37]NC2C=CC(C(O)=O)=CC=2)=[CH:35][CH:34]=1)([OH:32])=[O:31].[H-].[Na+].Br[CH2:53]CCCCC(Cl)=O>O(CCCC)CCCC>[CH3:53][O:32][C:30]([C:33]1[CH:49]=[CH:48][C:36]([CH2:37][N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)[C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][Br:18])=[CH:35][CH:34]=1)=[O:31]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 898486-Bromohexanoyl chlorideHCID 16086969HCID 16086969, compoundHCID 65347961HCID 65347961, compound

Product 1

HCID 16086950HCID 16086950, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

Following the reaction instructions for the production of compound 19a, the amine 15b (856 mg, 2.86 mmol) is first added to a suspension of sodium hydride (60% in mineral oil; 126 mg, 3.15 mmol) in anhydrous n-Bu2O (12 ml) and the resulting mixture is then added with 6-bromohexanoic acid chloride (0.51 ml, 3.43 mmol). The crude product that is obtained after processing is purified through column chromatography (silica gel, ethyl acetate/petroleum ether 1:2). 1.24 g (91%) of compound 19b are obtained as a colorless. Melting point. 190-191° C.; IR (Film) 2970, 2920, 2840, 1705, 1645, 1590 cm−1; 1H-NMR (CDCl3) δ 8.02 (d, 8.6 Hz, 2H), 7.94 (d, 8.4 Hz, 2H), 7.25 (d, 8.4 Hz, 2H), 7.05 (d, 8.4 Hz, 2H), 4.95 (s, 2H), 3.92 (s, 3H), 3.90 (s, 3H), 3.36 (t, 6.7 Hz, 2H), 2.11 (t, 7.4 Hz, 2H), 1.85-1.72 (m, 2H), 1.71-1.57 (m, 2H), 1.42-1.29 (m, 2H); MS (FD) m/z 477 (M+ for Br81), 475 (M+ for Br79).

Workup

  1. customThe crude product that is obtained after processing
  2. customis purified through column chromatography (silica gel, ethyl acetate/petroleum ether 1:2)

Sources & evidence

ORD record
ord-a5021e9fefb64f1e9d41abe6528187c5
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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