Triethylamine → HCID 57786563, compound

HRID 1669218Notes

Reaction equation

HRID 1669218 reaction equation
[O-:1][N+:2]1[C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:6]=2[N:5]=[C:4]([CH2:15][CH2:16][CH2:17][OH:18])[N:3]=1)[CH2:12][CH2:11][CH2:10]3.Cl.[CH3:20][N:21]([CH3:28])[CH2:22][CH2:23][CH2:24][C:25](O)=[O:26].C1CCC(N=C=NC2CCCCC2)CC1.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:20][N:21]([CH3:28])[CH2:22][CH2:23][CH2:24][C:25]([O:18][CH2:17][CH2:16][CH2:15][C:4]1[N:3]=[N+:2]([O-:1])[C:7]2[CH:8]=[C:9]3[C:13]([CH2:12][CH2:11][CH2:10]3)=[CH:14][C:6]=2[N:5]=1)=[O:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 119516443-(1-Oxido-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazin-3-yl)-1-propanolHCID 126916404-(Dimethylamino)butyric acid hydrochloride

Product 1

HCID 57786563HCID 57786563, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of alcohol 70 (100 mg, 0.41 mmol), 4-(dimethylamino)butanoic acid hydrochloride (68 mg, 0.41 mmol), DCC (93 mg, 0.45 mmol), DMAP (5 mg, 0.04 mmol) and Et3N (0.06 mL, 0.41 mmol) in DCM (20 mL) was stirred at 20° C. for 16 h. The solvent was evaporated and the residue purified by chromatography, eluting with a gradient (0-10%) of MeOH/20% EtOAc/DCM, to give the ester 309 (137 mg, 94%) as a pale-brown oil: 1H NMR δ 8.25 (s, 1H, H-9), 7.74 (s, 1H, H-5), 4.21 (t, J=6.3 Hz, 2H, CH2O), 3.06-3.15 (m, 6H, H-6, H-8, CH2), 2.73 (br s, 2H, H-7), 2.56 [s, 6H, N(CH3)2], 2.37 (t, J=7.0 Hz, 2H, CH2), 2.18-2.29 (m, 4H, CH2), 1.92-1.99 (m, 2H, CH2); 13C NMR δ 172.6, 164.9, 154.9, 149.1, 147.4, 132.3, 122.7, 114.2, 63.7, 57.7, 43.9 (2), 33.6, 33.2, 32.8, 31.3, 26.8, 25.7, 21.0; HRMS calcd for C19H26N4O3 (M+) m/z 358.2005, found 358.2006.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography
  3. washeluting with a gradient (0-10%) of MeOH/20% EtOAc/DCM

Sources & evidence

ORD record
ord-06a97dc2b6ac42baada8ac8ac10457c6
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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