Triethylamine → HCID 15819031, compound

HRID 1077822Notes

Reaction equation

HRID 1077822 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.Cl[C:17]([N:19]1[CH2:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH:25]=2)[CH2:20]1)=[O:18]>O1CCCC1>[CH:33]1([O:32][C:26]2[CH:25]=[C:24]([CH:21]3[CH2:22][CH2:23][N:19]([C:17]([NH:1][CH2:2][C:3]4[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=4)=[O:18])[CH2:20]3)[CH:29]=[CH:28][C:27]=2[O:30][CH3:31])[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 15819032HCID 15819032, compound

Product 1

HCID 15819031HCID 15819031, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

216 mg of 3-(aminomethyl) pyridine and 202 mg of triethylamine were dissolved in 5 ml of tetrahydrofuran. During agitation at a cold temperature, a solution obtained by dissolving 545 mg of 1-chloroformyl-3-(3-cyclopentyloxy-4-methoxyphenyl) pyrrolidine in 3 ml of tetrahydrofuran was added in drops. After dropping, agitation was continued for 6 hours at a room temperature. Thereafter, the agitated solution was poured into ice water and then extracted with ethyl acetate. After organic layers were cleaned by water and dried over magnesium sulfate, it was concentrated under a reduced pressure. The residue was purified by means of the silica gel column chromatography to obtain 432 mg of Compound No. 22 in Table 1.

Workup

  1. customDuring agitation at a cold temperature, a solution obtained
  2. additionwas added in drops
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate, it
  5. concentrationwas concentrated under a reduced pressure
  6. customThe residue was purified by means of the silica gel column chromatography

Sources & evidence

ORD record
ord-b7afb81dc3304437b7888b25487764b3
Source dataset
uspto-grants-1996_08
Patent number
US05545647

Reaction notes

Loading…