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

HRID 1893389Notes

Reaction equation

HRID 1893389 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-8a0f130b3c1145bd92109f14b27647aa
Source dataset
uspto-grants-2013_08
Patent number
US08513241B2

Reaction notes

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