1-Pyrrolidineethanamine → HCID 136341002, compound

HRID 888961Notes

Reaction equation

HRID 888961 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.C([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])C.Cl.C[N:18]([CH3:27])[CH2:19][CH2:20][CH2:21][N:22]=C=NCC.O.ON1[C:34]2[CH:35]=CC=C[C:33]=2[N:32]=N1.CN([CH:42]=[O:43])C>>[CH3:27][N:18]1[C:19]([C:12]2[NH:11][C:14]3[C:15](=[N:32][CH:33]=[CH:34][CH:35]=3)[CH:13]=2)=[CH:20][C:21]([C:42]([NH:1][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][CH2:6][CH2:5]2)=[O:43])=[N:22]1

Participants

6

Reactant 5

HCID 13441-PyrrolidineethanamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 136341002HCID 136341002, compoundYield 9%

Procedure

The intermediate 15 (120 mg, 0.5 mmol) and N-(2-amino-ethyl)pyrrolidine (59 mg, 0.5 mmol) was dissolved in DMF (4 mL). triethylamine (260 mg, 2.6 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (98 mg, 0.5 mmol) and 1-hydroxybenzotriazole monohydrate (39 mg, 0.3 mmol) were successively added to the resulting mixture at the room temperature. The obtained mixture was stirred at room temperature for 2 days. The solvent was removed under reduced pressure, and the resulting crude product was purified with a preparative HPLC system (the purification apparatus B) to afford crystalline product (15 mg, 9% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting crude product was purified with a preparative HPLC system (the purification apparatus B)

Sources & evidence

ORD record
ord-0094f585a7f8490d86165d024a1c8c28
Source dataset
uspto-grants-2012_08
Patent number
US08252790B2

Reaction notes

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