Diisopropylethylamine → HCID 66811847, compound

HRID 1869300Notes

Reaction equation

HRID 1869300 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([I:9])[CH:8]=1)[NH2:5].[CH3:10][Si:11]([CH3:27])([CH3:26])[CH2:12][CH2:13][O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])=[O:16].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOCC>[CH3:26][Si:11]([CH3:10])([CH3:27])[CH2:12][CH2:13][O:14][C:15](=[O:16])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:24])[NH:5][C:4]1[CH:3]=[C:2]([I:1])[CH:8]=[C:7]([I:9])[CH:6]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 121342543,5-DIIODOANILINEHCID 86600508HCID 86600508, compound

Product 1

HCID 66811847HCID 66811847, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3,5-Diiodoaniline [Dininno, F.; Guthikonda, R. N.; Schmitt, S. M. 1994 U.S. Pat. No. 5,292,879 A] (1 g, 2.90 mmol), 6-(2-Trimethylsilanyl-ethoxycarbonylamino)-hexanoic acid (1 g, 3.77 mmol) in DMF (12 ml) were added DIPEA (0.9 ml, 5.8 mmol) and HATU (1.65 g, 4.35 mmol). The mixture was stirred for overnight at room temperature. The reaction mixture was diluted with Et2O. To the mixture was added sat.NaHCO3 and then separated. The aqueous phase was extracted with Et2O (3×40 ml). The combined extraction were washed with 5% HCl (30 ml), H2O (50 ml), sat.NaHCO3 (30 ml), and Brine (30 ml), and finally dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by silica gel column with (Hexane:EtOAc=6:4) to afford 21 (1 g, 59%) as a colorless powder. 1H NMR (300 MHz, (CD3)2SO): δ 0.09 (S, 9H), 0.84 (t, J=2.1 Hz, 2H), 1.34 (m, 2H), 1.40 (m, 2H), 1.50 (m, 2H), 2.41 (t, J=1.8 Hz, 2H), 2.47 (m, 2H), 2.89 (m, 2H), 4.01 (t, 2H), 6.92 (bt, 1H), 7.68 (m, 1H), 7.99 (m, 2H); 13C NMR (75 MHz, (CD3)2SO): δ −0.72, 18.0, 25.2, 26.4, 29.9, 36.9, 61.9, 96.4, 127.0, 139.0, 142.3, 156.9, 172.2; IR (film): 3326, 2853, 2361, 1687, 1541, 1450, 1249, 837 cm−1; MS: (ESI)) [M+Na]+ 624.9

Workup

  1. additionTo the mixture was added
  2. customNaHCO3 and then separated
  3. extractionThe aqueous phase was extracted with Et2O (3×40 ml)
  4. extractionThe combined extraction
  5. washwere washed with 5% HCl (30 ml), H2O (50 ml)
  6. dry with materialNaHCO3 (30 ml), and Brine (30 ml), and finally dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude was purified by silica gel column with (Hexane:EtOAc=6:4)

Sources & evidence

ORD record
ord-53ce7ed06d694f4db7d0348741a7ab14
Source dataset
uspto-grants-2009_12
Patent number
US07638544B2

Reaction notes

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