Diisopropylethylamine → 3,4-Dihydropyrazino[1,2-a]indol-1(2H)-one

HRID 221229Notes

Reaction equation

HRID 221229 reaction equation
[N+]([C:4]1[CH:12]=[CH:11][C:10]2[N:9]3[CH:13](CC(O)=O)[CH2:14][NH:15][C:16](=[O:17])[C:8]3=[CH:7][C:6]=2[CH:5]=1)([O-])=O.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O>[C:16]1(=[O:17])[C:8]2=[CH:7][C:6]3[CH:5]=[CH:4][CH:12]=[CH:11][C:10]=3[N:9]2[CH2:13][CH2:14][NH:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 44122311HCID 44122311, compound

Product 1

HCID 149257583,4-Dihydropyrazino[1,2-a]indol-1(2H)-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of the acid derivative of formula (VII) (57 mg, 0.2 mmol, 2 eq), DIPEA (0.068 ml, 0.39 mmol, 4 eq.), PyBOP (102.75 mg, 0.2 mmol, 2 eq.) in dry DMA (2.0 ml) was stirred for 30 min then was added to resin of example 6 (0.1 mmol, 1 eq.) and the final suspension was shaken for 20 h at 25° C. The resin was washed sequentially with DMF (1 ml), DCM (1 ml), DMF (1 ml), DCM (1 ml), MeOH (1 ml), water (1 ml), MeOH (1 ml), DCM (1 ml), MeOH (1 ml), DCM (1 ml), MeOH (1 ml), MTBE (1 ml, 2 cycles) and then air dried.

Workup

  1. washThe resin was washed sequentially with DMF (1 ml), DCM (1 ml), DMF (1 ml), DCM (1 ml), MeOH (1 ml), water (1 ml), MeOH (1 ml), DCM (1 ml), MeOH (1 ml), DCM (1 ml), MeOH (1 ml), MTBE (1 ml, 2 cycles)
  2. customair dried

Sources & evidence

ORD record
ord-7948d4c1942941e88ebc9e98f767ebe4
Source dataset
uspto-grants-2012_06
Patent number
US08207165B2

Reaction notes

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