Triethylamine → HCID 59767739, compound

HRID 1445707Notes

Reaction equation

HRID 1445707 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][C:13]2[N:18]=[C:17]([C:19]([OH:21])=O)[CH:16]=[CH:15][CH:14]=2)=[N:4][NH:3]1.C(N(CC)CC)C.C(OC([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)=O)(C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[N:36]1([C:19]([C:17]2[N:18]=[C:13]([CH2:12][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2](=[O:1])[NH:3][N:4]=3)[CH:14]=[CH:15][CH:16]=2)=[O:21])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59767751HCID 59767751, compound

Product 1

HCID 59767739HCID 59767739, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-pyridine-2-carboxylic acid (ivb)(0.3 g, 1.1 mmol), triethylamine (0.3 ml, 2.1 mmol), tert-butyl-1-piperazine carboxylate (0.23 g, 1.3 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.5 g, 1.3 mmol) in dimethylformamide (10 ml) was stirred for 18 hours. The reaction mixture was precipitated on the addition of water (50 ml) and air-dried. The white precipitate was dissolved in ethanol (3 ml) and 12 M hydrochloric acid (6 ml) was added to the solution and the reaction was stirred for 30 minutes. The reaction was then concentrated in vacuo, redissolved in water (10 ml) and washed with dichloromethane (2×10 ml). The aqueous layer was basified with ammonium hydroxide and extracted into dichloromethane (2×10 ml). The combined organic layers was dried with MgSO4, filtered and evaporated to yield the expected product (va) as a pink solid (0.23 g, 73%). m/z [M+1]+ 250 (96% purity)

Workup

  1. customThe reaction mixture was precipitated on the addition of water (50 ml)
  2. customair-dried
  3. dissolutionThe white precipitate was dissolved in ethanol (3 ml)
  4. addition12 M hydrochloric acid (6 ml) was added to the solution
  5. stirringthe reaction was stirred for 30 minutes
  6. concentrationThe reaction was then concentrated in vacuo
  7. dissolutionredissolved in water (10 ml)
  8. washwashed with dichloromethane (2×10 ml)
  9. extractionextracted into dichloromethane (2×10 ml)
  10. dry with materialThe combined organic layers was dried with MgSO4
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-faf8b6a8d7e540178be7bdc5bace9387
Source dataset
uspto-grants-2010_02
Patent number
US07666870B2

Reaction notes

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