Diisopropylethylamine → HCID 45140182, compound

HRID 574284Notes

Reaction equation

HRID 574284 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2.C(N(C(C)C)CC)(C)C.[N:24]1([CH2:30][CH2:31][N:32]([CH2:44][CH2:45][CH3:46])[CH:33]2[CH2:42][C:41]3[CH:40]=[C:39]([OH:43])[CH:38]=[CH:37][C:36]=3[CH2:35][CH2:34]2)[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(Cl)(Cl)Cl>[OH:43][C:39]1[CH:40]=[C:41]2[C:36]([CH2:35][CH2:34][CH:33]([N:32]([CH2:44][CH2:45][CH3:46])[CH2:31][CH2:30][N:24]3[CH2:25][CH2:26][N:27]([CH2:3][C:4]4[CH:13]=[CH:12][C:11]([OH:14])=[C:10]5[C:5]=4[CH:6]=[CH:7][CH:8]=[N:9]5)[CH2:28][CH2:29]3)[CH2:42]2)=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)2×HCID 45139978HCID 45139978, compound

Product 1

HCID 45140182HCID 45140182, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 5-chloromethyl-8-quinolinol hydrochloride, 11 (0.20 g, 0.86 mmol) and diisopropylethylamine (0.3 mL, 1.73 mmol, 2.2 equiv) in 25 mL CHCl3 at 0° C. was added 9a (0.25 g, 0.78 mmol). The mixture was stirred for 24 h at room temperature. CHCl3 (100 mL) was added and the solution obtained was washed with 10% NaHCO3, brine, and then dried over Na2SO4. The solution was filtered and evaporated to dryness. The residue was made hydrochloride salt and crystallized from ethanol to yield 12a as yellow solid (0.28 g, 57.3%). 1H NMR of HCl salt (400 MHz, DMSO-d6) δ ppm 0.88-0.99 (m, 3H), 1.79-1.81 (bs, 4H), 2.298 (bs, 1H), 2.476-2.48 (m, 2H), 2.74 (s, 2H), 2.96-3.02 (t, 1H, J=12 Hz), 3.122 (bs, 3H), 3.34-3.65 (m, 12H), 6.51-6.56 (m, 2H), 6.86-6.88 (d, 1H, J=8 Hz), 7.50-7.52 (d, 1H, J=8 Hz), 7.997-8.008 (m, 2H); 9.06-9.07 (d, 1H, J=4 Hz); 9.49-9.51 (d, 1H, J=8 Hz). The hydrochloride salt mp 242-242° C. Analysis calculated for (C29H40.6N4O3.3, 4HCl) C, H, N.

Workup

  1. customthe solution obtained
  2. washwas washed with 10% NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was filtered
  5. customevaporated to dryness
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-db05b0756e68454b96885232b270ef71
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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