Triethylamine → HCID 58465801, compound

HRID 1842455Notes

Reaction equation

HRID 1842455 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH2:48]1[NH:54][CH2:53][CH2:52][CH2:51][N:50]2[CH:55]=[C:56]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH:57]=[C:49]12>CN(C=O)C.C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:54]1[CH2:53][CH2:52][CH2:51][N:50]2[CH:55]=[C:56]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH:57]=[C:49]2[CH2:48]1)=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 814531-Methyl-2-pyrrolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67438051HCID 67438051, compound

Product 1

HCID 58465801HCID 58465801, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a vial containing N-methylpyrrole-2-carboxylic acid (0.025 g, 0.2 mmol) was added HATU (0.076 g, 0.2 mmol), DCM (2 mL), and triethylamine (0.112 mL, 0.8 mmol). The solution was stirred at rt for 30 min then ethyl 2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine-8-carboxylate 2,2,2-trifluoroacetate (0.0644 g, 0.2 mmol) in DMF (0.5 mL) was added. The mixture was stirred at rt for 2 h. The reaction was quenched by addition of DCM (1 mL), sat. NaHCO3 solution (0.5 mL), and water (1 mL). After separation, the aqueous layer was extracted with DCE (2×3 mL). The combined organic layers were concentrated to give crude ethyl 2-(1-methyl-1H-pyrrole-2-carbonyl)-2,3,4,5-tetrahydro-1H-pyrrolo[1,2-a][1,4]diazepine-8-carboxylate.

Workup

  1. stirringThe mixture was stirred at rt for 2 h
  2. customThe reaction was quenched by addition of DCM (1 mL), sat. NaHCO3 solution (0.5 mL), and water (1 mL)
  3. customAfter separation
  4. extractionthe aqueous layer was extracted with DCE (2×3 mL)
  5. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-edf14c3a555f434fa81d877a44a71865
Source dataset
uspto-grants-2015_02
Patent number
US08946223B2

Reaction notes

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