Diethylamine → HCID 67343410, compound

HRID 1850091Notes

Reaction equation

HRID 1850091 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])[CH:16]=[CH:17][C:18]=2O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N([OH:39])N=NC=2C=1.[CH3:40][CH2:41][N:42]([CH2:45][CH3:46])[CH2:43]C.N(CC)CC.CCN=C=NCCCN(C)C.Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:14]=[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:27])([F:29])[F:28])[CH:16]=[CH:17][C:18]=2[C:43](=[O:39])[N:42]([CH2:45][CH3:46])[CH2:41][CH3:40])[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 6

HCID 8021DiethylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67342893HCID 67342893, compound

Product 1

HCID 67343410HCID 67343410, compoundYield 832.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the title compound of Step B (0.09 g, 0.21 mmol) in CH2Cl2 (2 mL) was added HOBt (0.003 g, 0.02 mmol), Et3N (0.03 mL, 0.02 g, 0.23 mmol), Et2NH (0.02 g, 0.02 mL, 0.23 mmol) and EDC.HCl (0.04 g, 0.23 mmol). After 18 h, saturated NaHCO3 (aq.) was added and the reaction extracted with CH2Cl2 (2×). The combined organics were dried. Silica gel chromatography (0-60% EtOAc in hexanes) gave 0.082 g (80% yield) of the title compound. MS (ESI): mass calcd. for C26H31F3N2O4, 492.22. m/z found, 437.2 [M-56]+, 493.2 [M+H]+. 1H NMR (CDCl3): 7.75 (d, J=7.7 Hz, 1H), 7.58 (t, J=7.4 Hz, 1H), 7.50 (t, J=7.7 Hz, 1H), 7.32 (d, J=7.5 Hz, 1H), 7.28 (d, J=7.6 Hz, 1H), 6.99 (dd, J=7.6, 1.2 Hz, 1H), 6.51 (s, 1H), 4.93-4.83 (m, 1H), 4.25 (dd, J=9.6, 6.5 Hz, 2H), 4.01 (s, 1H), 3.94 (s, 1H), 3.79 (s, 1H), 3.41 (s, 1H), 3.21 (q, J=7.1 Hz, 2H), 1.44 (s, 9H), 1.28 (t, J=7.1 Hz, 3H), 1.10 (t, J=7.1 Hz, 3H).

Workup

  1. extractionthe reaction extracted with CH2Cl2 (2×)
  2. customThe combined organics were dried

Sources & evidence

ORD record
ord-70f6cf15b03b4cae923fb2c7a00cee2e
Source dataset
uspto-grants-2015_02
Patent number
US08957059B2

Reaction notes

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