Triethylamine → HCID 67874578, compound

HRID 1418690Notes

Reaction equation

HRID 1418690 reaction equation
[OH:1][CH:2]([C:5]1[CH:21]=[C:20]2[N:8]([CH2:9][C:10]3[C:11]2=[N:12][C:13]2[C:18]([CH:19]=3)=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7](=[O:22])[C:6]=1[CH3:23])[CH2:3][CH3:4].[CH3:24][C:25]([CH3:45])([O:27][C:28]([NH:30][CH2:31][CH2:32][C:33](OC1C=CC([N+]([O-])=O)=CC=1)=[O:34])=[O:29])[CH3:26].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCCl>[CH3:23][C:6]1[C:7](=[O:22])[N:8]2[C:20](=[CH:21][C:5]=1[CH:2]([O:1][C:33](=[O:34])[CH2:32][CH2:31][NH:30][C:28]([O:27][C:25]([CH3:26])([CH3:24])[CH3:45])=[O:29])[CH2:3][CH3:4])[C:11]1=[N:12][C:13]3[C:18]([CH:19]=[C:10]1[CH2:9]2)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 613105HCID 613105, compoundHCID 4174151Boc-beta-alanine 4-nitrophenyl ester2×

Product 1

HCID 67874578HCID 67874578, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture containing (±)-7-(1-hydroxypropyl)-8-methylindolizino[1,2-b]quinolin-9(11H)-one (61.2 mg, 0.20 mmol), 4-dimethylaminopyridine (7.4 mg, 0.06 mmol), 4-nitrophenyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]propionate (248 mg, 0.80 mmol) and dry triethylamine (222 mL, 1.60 mmol) in 1,2-dichloroethane (5 mL) under an argon atmosphere was heated at reflux for 5 d. Thin layer chromatographic analysis at this time indicated that the reaction was incomplete, so the mixture was transferred to a pressure bottle and heated at 90°-95° C. for 1 d. Afterwards, additional 4-nitrophenyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]propionate (248 mg, 0.80 mmol) and dry triethylamine (222 mL, 1.60 mmol) were added, and heating was continued for 13 d. The mixture was then purified by flash chromatography eluting with a solvent gradient of 0-3% MeOH/CH2Cl2. The material that was isolated was recrystallized from Et2O and dried in vacuo to afford the title compound, mp 155°-8° C. 1H NMR (CDCl3) d 8.35 (s, 1H), 8.22 (d, J=8.6 Hz, 1H), 7.91 (d, J=7.2 Hz, 1H), 7.81 (m, 1H), 7.63 (m, 1H), 7.32 (s, 1H), 5.90 (dd, J=7.7, 6.1 Hz, 1H), 5.26 (s, 2H), 5.02 (br s, 1H), 3.44 (m, 2H), 2.66 (q, J=5.8 Hz, 2H), 2.02-1.80 (m, 2H), 1.38 (s, 9H), 0.98 (t, J=7.4 Hz, 3H). Anal. Calcd for C27H31N3O5.1/5 H2O: C, 67.40; H, 6.58; N, 8.73. Found: C, 67.78; H, 6.48; N, 8.35.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 d
  3. temperatureheated at 90°-95° C. for 1 d
  4. temperatureheating
  5. customThe mixture was then purified by flash chromatography
  6. washeluting with a solvent gradient of 0-3% MeOH/CH2Cl2
  7. customThe material that was isolated
  8. customwas recrystallized from Et2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-651cf774dcdd4106894d2c000e5ff2f0
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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