Triethylamine → HCID 86666747, compound

HRID 1911831Notes

Reaction equation

HRID 1911831 reaction equation
[Si:1]([O:8][C@H:9]([C:38]1[CH:39]=[N:40][C:41]([Cl:44])=[CH:42][CH:43]=1)[C@H:10]([NH:25]C(OCC1C=CC(OC)=CC=1)=O)[CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C>ClCCl>[NH2:25][C@@H:10]([C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:38]1[CH:39]=[N:40][C:41]([Cl:44])=[CH:42][CH:43]=1)[CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86666748HCID 86666748, compound

Product 1

HCID 86666747HCID 86666747, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the title compound from Step A (83.0 g, 0.13 mol) in dichloromethane (400 mL) was added triethylamine (20 mL) and the resulting mixture was stirred for 3 h. The reaction mixture turned to dark red color. All volatiles were evaporated and the residue was diluted with water and based by NaHCO3. It was then extracted with dichloromethane (3×250 mL). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography with dichloromethane/methanol=20:1 to afford 47.0 g (77%) of the title compound as yellow gum. 1H NMR (400 MHz, CDCl3): δ 8.35 (s, 1H), 7.95 (d, J=8.6 Hz, 2H), 7.63 (d, J=7.8 Hz, 1H), 7.41 (d, J=8.6 Hz, 2H), 7.31 (d, J=8.6 Hz, 1H), 4.55 (d, J=4.7 Hz, 1H), 3.93 (s, 3H), 2.96-2.93 (m, 1H), 2.64-2.53 (m, 2H), 1.71-1.68 (m, 1H), 1.52-1.41 (m, 3H), 0.90 (s, 9H), 0.20 (s, 3H), 0.00 (s, 3H). MS: m/z. (EST) 473 (M+1).

Workup

  1. customAll volatiles were evaporated
  2. additionthe residue was diluted with water
  3. extractionIt was then extracted with dichloromethane (3×250 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography with dichloromethane/methanol=20:1

Sources & evidence

ORD record
ord-8d34edc4a6834458a2ba0404d18b4ed6
Source dataset
uspto-grants-2013_12
Patent number
US08604038B2

Reaction notes

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