Triethylamine → HCID 118159185, compound

HRID 713212Notes

Reaction equation

HRID 713212 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH:8]=[N:9][CH:10]=[CH:11][C:5]2=[N:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[CH2:14][CH2:13]1.CCN(CC)CC.Cl.[O:35]1[CH2:39][CH2:38][C@H:37]([NH2:40])[CH2:36]1>CN(C=O)C>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[CH2:18][N:15]1[CH2:16][CH2:17][N:12]([C:3]2[N:4]=[C:5]3[CH:11]=[CH:10][N:9]=[CH:8][C:6]3=[N:7][C:2]=2[NH:40][C@H:37]2[CH2:38][CH2:39][O:35][CH2:36]2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 1181593003-Chloro-2-(4-(2,4-difluorobenzyl)piperazin-1-yl)pyrido[3,4-b]pyrazine

Product 1

HCID 118159185HCID 118159185, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-chloro-2-(4-(2,4-difluorobenzyl)piperazin-1-yl)pyrido[3,4-b]pyrazine (3.0 g, 7.98 mmol) and Et3N (10 mL, 71.7 mmol) in DMF (30 mL) was added (S)-tetrahydrofuran-3-amine hydrochloride (2.96 g, 23.95 mmol) at room temperature. The mixture was stirred at 60° C. for 16 h then separated between water and EtOAc. The organic layer was washed with brine and water, then dried and concentrated to yield the crude residue, which was purified by column to give the title compound (800 mg) as a yellow oil. ESI-MS m/z [M+H]+ 427.1.

Workup

  1. customthen separated between water and EtOAc
  2. washThe organic layer was washed with brine and water
  3. customdried
  4. concentrationconcentrated
  5. customto yield the crude residue, which
  6. customwas purified by column

Sources & evidence

ORD record
ord-77e18f0072214c38bd2e2ac9b03712d6
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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