Diisopropylethylamine → HCID 71730367, compound

HRID 1056205Notes

Reaction equation

HRID 1056205 reaction equation
C([NH:5]C1C(C)=NC2C(N=1)=C(C1NC3CN[C:23](=[O:24])C=3C=1)C=CC=2)(C)(C)C.Cl.[NH2:27][CH2:28][C:29]1[NH:30][C:31]([C:37]2[CH:46]=[CH:45][CH:44]=[C:43]3[C:38]=2[N:39]=[C:40]([NH:48][C:49]([CH3:52])([CH3:51])[CH3:50])[C:41]([CH3:47])=[N:42]3)=[CH:32][C:33]=1[C:34]([OH:36])=O.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>C(Cl)Cl.CN(C=O)C>[NH3:5].[CH3:23][OH:24].[C:49]([NH:48][C:40]1[C:41]([CH3:47])=[N:42][C:43]2[C:38]([N:39]=1)=[C:37]([C:31]1[NH:30][C:29]3[CH2:28][NH:27][C:34](=[O:36])[C:33]=3[CH:32]=1)[CH:46]=[CH:45][CH:44]=2)([CH3:52])([CH3:51])[CH3:50]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 71730367HCID 71730367, compoundHCID 89783476HCID 89783476, compound

Product 2

HCID 21705897Ammonia methanolYield 0%HCID 71730367HCID 71730367, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Preparation 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (334). To a 100-mL round-bottomed flask was added 2-(aminomethyl)-5-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-1H-pyrrole-3-carboxylic acid hydrochloride (334c) (0.21 g, 0.55 mmol), DCM (10 mL), DMF (10 mL), DIEA (0.29 mL, 1.65 mmol), and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (0.34 g, 0.66 mmol) (Sigma-Aldrich Chemical Company, Inc.). The reaction mixture was stirred at RT for 30 min, concentrated to half of its volume, and diluted with EtOAc (10 mL). The organic extract was washed with sat NaHCO3 (5 mL), dried over Na2SO4, and concentrated. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluted first with 30% EtOAc in hexanes, and then with a gradient of 0-4% 2 M NH3/MeOH in DCM to provide 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (334) (97 mg, 52% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.08 (br. s., 1H), 7.82 (d, J=7.24 Hz, 1H), 7.63 (d, J=8.02 Hz, 1H), 7.53 (s, 1H), 7.37 (t, J=7.73 Hz, 1H), 6.94 (s, 1H), 6.02 (s, 1H), 4.29 (s, 2H), 2.58 (s, 3H), 1.55 (s, 9H). m/z (ESI, +ve) 336.2 (M+H)+.

Workup

  1. concentrationconcentrated to half of its volume
  2. additiondiluted with EtOAc (10 mL)
  3. extractionThe organic extract
  4. washwas washed with sat NaHCO3 (5 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude material was absorbed onto a plug of silica gel
  8. custompurified by chromatography through a Redi-Sep pre-packed silica gel column (12 g)
  9. washeluted first with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-db01a97807e9474896c5d9db4f1306b9
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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