Triethylamine → HCID 25172542, compound

HRID 926234Notes

Reaction equation

HRID 926234 reaction equation
[S:1](Cl)([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:18]([O:20][CH:21]([O:26][CH2:27][CH3:28])[CH2:22][CH2:23][CH2:24][NH2:25])[CH3:19].CCN(CC)CC>C(Cl)Cl>[CH2:27]([O:26][CH:21]([O:20][CH2:18][CH3:19])[CH2:22][CH2:23][CH2:24][NH:25][S:1]([C:4]1[C:16]2[C:8](=[C:9]([N:10]([CH3:12])[CH3:11])[CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11801Dansyl chlorideHCID 806724,4-Diethoxybutylamine

Product 1

HCID 25172542HCID 25172542, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of dansyl chloride (270 mg, 1.00 mmol) in CH2Cl2 (10 mL) was added 4-aminobutyraldehyde diethyl acetal (237 μL, 1.20 mmol) and Et3N (170 μL, 1.20 mmol). The solution was stirred for 1 h at 25° C. and was then evaporated to dryness under reduced pressure. The material left was processed and purified under conditions identical to those described for the processing and purification of 11. Fractions containing the product were collected and evaporated to dryness under low pressure affording 13 (366 mg, 930 μmol) as a solid in a yield of 93%. 1H NMR (300 MHz, DMSO-d6): δ 8.45 (dt, J=8.5, 1.1 Hz, 1H), 8.30 (dt, J=8.8, 0.9 Hz, 1H), 8.09 (dd, J=7.3, 1.2 Hz, 1H), 7.89 (t, J=5.5 Hz, 1H), 7.61 (t, J=8.5 Hz, 1H), 7.58 (t, J=8.5 Hz, 1H), 7.25 (dd, J=7.6, 0.7 Hz, 1H), 4.19 (t, J=5.3 Hz, 1H), 3.36 (m, 2H), 3.23 (m, 2H), 2.81 (s, 6H), 2.77 (t, J=5.5 Hz, 2H), 1.31 (m, 4H), 0.99 (t, J=7.0 Hz, 6H). 13C NMR (75 MHz, DMSO-d6): δ 151.2, 136.1, 129.2, 128.9, 128.1, 127.7, 123.5, 119.1, 114.9, 101.6, 60.2, 44.9, 42.2, 30.1, 24.4, 15.1. +ESI-HRMS: Calcd for C20H30N2O4S [M+H]+ 395.1999. found 395.2000.

Workup

  1. customwas then evaporated to dryness under reduced pressure
  2. waitThe material left
  3. custompurified under conditions identical to
  4. customthose described for the processing and purification of 11
  5. additionFractions containing the product
  6. customwere collected
  7. customevaporated to dryness under low pressure

Sources & evidence

ORD record
ord-847370e79f1246d8a37de7f07949b699
Source dataset
uspto-grants-2016_03
Patent number
US09284343B2

Reaction notes

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