Diethylamine → Diethylamine

HRID 1418703Notes

Reaction equation

HRID 1418703 reaction equation
[NH:1]([CH2:4][CH3:5])[CH2:2][CH3:3].C1C2C(COC([NH:23][CH2:24][P:25]([OH:50])([O:27][CH:28]([C:31]3[CH:47]=[C:46]4[N:34]([CH2:35][C:36]5[C:37]4=[N:38][C:39]4[C:44]([CH:45]=5)=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33](=[O:48])[C:32]=3[CH3:49])[CH2:29][CH3:30])=[O:26])=O)C3C(=CC=CC=3)C=2C=CC=1>O>[NH2:23][CH2:24][P:25]([OH:50])([O:27][CH:28]([C:31]1[CH:47]=[C:46]2[N:34]([CH2:35][C:36]3[C:37]2=[N:38][C:39]2[C:44]([CH:45]=3)=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33](=[O:48])[C:32]=1[CH3:49])[CH2:29][CH3:30])=[O:26].[NH:1]([CH2:4][CH3:5])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 86753928HCID 86753928, compound

Product 2

HCID 8021DiethylamineHCID 53659887HCID 53659887, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of Et2NH (10 mL) and (±)-7-[1-[[[[[(9-fluorenylmethoxy)carbonyl]amino]methyl]hydroxyphosphinyl]oxy]propyl]-8-methylindolizino[1,2-b]quinolin-9(11H)-one (328 mg, 0.51 mmol) was stirred at room temperature in a capped vial for 3 h. The reaction mixture was stripped to dryness, and H2O was added. The this partial solution was extracted with EtOAc, filtered and lyophilized to give a viscous oil which was triturated with CH3CN to produce a golden solid. The solid was dissolved in H2O and lyophilized to give the title compound as a partial Et2NH salt. 1H NMR (CDCl3 /MeOH-d4) d 8.49 (s, 1H), 8.12 (d, J=8.7 Hz, 1H), 8.00 (d, J=8.3 Hz, 1H), 7.84 (m, 1H), 7.69 (overlapping s and m, 2H), 5.59 (dd, J=14.9, 6.5 Hz, 1H), 5.27 (s, 2H), 2.98 (q, J=7.2 Hz, ~1.1H), 2.85 (dd, J=12.7, 2.6 Hz, 2H), 2.31 (s, 3H), 2.02-1.83 (m, 2H), 1.31 (t, I=7.3 Hz, ~1.8H), 1.05 (t, J=7.4 Hz, 3H). Anal. Calcd for C20H22N3O4P.1/4 C4H11N.5 H2O: C, 49.68; H, 6.90; N, 8.97. Found: C, 50.08; H, 6.49; N, 8.46.

Workup

  1. additionwas added
  2. extractionThe this partial solution was extracted with EtOAc
  3. filtrationfiltered
  4. customto give a viscous oil which
  5. customwas triturated with CH3CN
  6. customto produce a golden solid

Sources & evidence

ORD record
ord-1b58b9286fde41fe8984556039abf6ed
Source dataset
uspto-grants-1999_03
Patent number
US05883255

Reaction notes

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