Triethylamine → HCID 117988523, compound

HRID 63791Notes

Reaction equation

HRID 63791 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:21]3=[CH:30][C:31]([C:33](O)=[O:34])=[CH:32][N:20]3[N:19]=2)=[CH:14][CH:13]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>O.CN(C)C=O>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:21]3=[CH:30][C:31]([C:33]([N:3]([CH3:4])[CH3:2])=[O:34])=[CH:32][N:20]3[N:19]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117988541HCID 117988541, compound

Product 1

HCID 117988523HCID 117988523, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dimethylamine hydrochloride (686 mg, 8.4 mmol) was added to 30 mL of anhydrous N,N-dimethylformamide, and potassium carbonate (3.48 g, 25.2 mmol) was added and stirred for minutes at room temperature. Then compound 11a (4.2 mmol), HBTU (benzotriazole-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 4.77 g, 12.6 mmol), and triethylamine (2.9 mL, 21 mmol) were added and reacted overnight at room temperature under nitrogen atmosphere. The reaction mixture was poured into water and filtered. The filtrate was extracted once with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was combined with the filter cake. The crude product was purified by column chromatography (dichloromethane:methanol=100:1) to give white compound 12a (922 mg, 60.0%). m.p. 238-239° C. 1H NMR (300 MHz, CDCl3): δ 8.08 (d, J=8.6 Hz, 2H), 7.82 (d, J=1.4 Hz, 1H), 7.02 (d, J=1.4 Hz, 1H), 6.73 (d, J=8.6 Hz, 2H), 4.11 (t, J=4.4 Hz, 4H), 3.86 (t, J=4.4 Hz, 4H), 3.20 (br, s, 6H). MS (EI) m/e (%): 366 (M+, 100).

Workup

  1. additionwas added
  2. customreacted overnight at room temperature under nitrogen atmosphere
  3. filtrationfiltered
  4. extractionThe filtrate was extracted once with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude product was purified by column chromatography (dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-5a6318887e5a4183a2e52a928559add1
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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