Dichloromethane → HCID 89783535, compound

HRID 1056240Notes

Reaction equation

HRID 1056240 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[NH:5][C:6]([C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[N:14]=[C:15]([NH:23][CH:24]2[CH2:26][CH2:25]2)[C:16]([CH3:22])=[N:17]3)=[CH:7][C:8]=1[C:9](O)=[O:10].[CH2:27](Cl)Cl.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C>[CH3:22][C:16]1[C:15]([NH:23][C:24]2([CH3:27])[CH2:25][CH2:26]2)=[N:14][C:13]2[C:18](=[CH:19][CH:20]=[CH:21][C:12]=2[C:6]2[NH:5][C:4]3[CH2:3][NH:2][C:9](=[O:10])[C:8]=3[CH:7]=2)[N:17]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 89783619HCID 89783619, compound

Product 1

HCID 89783535HCID 89783535, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 25-mL round-bottomed flask was added 2-(aminomethyl)-5-(3-(cyclopropylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (363c) (0.19 g, 0.52 mmol), DCM (6 mL), DMF (6 mL), DIEA (0.27 mL, 1.57 mmol), and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.30 g, 0.58 mmol) (Sigma-Aldrich Chemical Company, Inc.). The reaction mixture was stirred at RT for 16 h, concentrated to half of its volume, and poured over water. The yellow solid obtained was filtered, washed with water, ether, and dried in a vacuum over at 50° C. for 16 h. 2-(2-Methyl-3-((1-methylcyclopropyl)amino)-quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (363) (0.13 g, 77% yield) was obtained a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.01 (dd, J=0.68, 7.53 Hz, 1H), 7.63 (s, 1H), 7.61 (dd, J=0.78, 8.02 Hz, 1H), 7.53 (s, 1H), 7.36 (t, J=7.73 Hz, 1H), 7.04 (d, J=1.17 Hz, 1H), 4.31 (s, 2H), 2.89 (br. s, 1H), 2.52 (s, 3H), 0.87-0.94 (m, 2H), 0.67-0.74 (m, 2H). m/z (ESI, +ve) 320.1 (M+H)+.

Workup

  1. concentrationconcentrated to half of its volume
  2. additionpoured over water
  3. customThe yellow solid obtained
  4. filtrationwas filtered
  5. washwashed with water, ether
  6. customdried in a vacuum over at 50° C. for 16 h

Sources & evidence

ORD record
ord-fdd3f51d8432452bba808a4db4576fe9
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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