Trifluoroacetic acid → HCID 89784036, compound

HRID 1056040Notes

Reaction equation

HRID 1056040 reaction equation
[CH3:1][C:2]1([CH3:35])[N:7]([C:8]2[CH:17]=[N:16][C:15]3[C:10](=[C:11]([C:18]4[NH:26][C:25]5[CH2:24][CH2:23][NH:22][C:21](=[O:27])[C:20]=5[CH:19]=4)[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:35])[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[C:8]1[CH:17]=[N:16][C:15]2[C:10]([N:9]=1)=[C:11]([C:18]1[NH:26][C:25]3[CH2:24][CH2:23][NH:22][C:21](=[O:27])[C:20]=3[CH:19]=1)[CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89784004HCID 89784004, compound

Product 1

HCID 89784036HCID 89784036, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3,3-dimethyl-4-(8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)piperazine-1-carboxylate (27 mg, 0.057 mmol) and TFA (4.36 μl, 0.057 mmol) in DCM (567 μl) was stirred at RT for 20 min. Purification by silica gel (100% DCM to 8% [2 M NH3 in MeOH]/DCM) provided 2-(3-(2,2-dimethylpiperazin-1-yl)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (19% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (s, 6H) 2.32-2.35 (m, 1H) 2.66-2.71 (m, 2H) 2.86 (t, J=6.94 Hz, 2H) 2.95-2.99 (m, 1H) 3.44 (td, J=6.75, 2.35 Hz, 2H) 3.60 (t, J=4.9 Hz, 2H) 6.96 (s, 1H) 7.09 (d, J=2.15 Hz, 1H) 7.52 (t, J=7.63 Hz, 1H) 7.73 (d, J=7.04 Hz, 1H) 7.92 (d, J=7.43 Hz, 1H) 8.81 (s, 1H) 11.71 (s, 1H). MS (ESI, pos. ion) m/z: 377.1 (M+1).

Workup

  1. customPurification by silica gel (100% DCM to 8% [2 M NH3 in MeOH]/DCM)

Sources & evidence

ORD record
ord-54c115f51f0b466e825395b8ffea89df
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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