Triethylamine → HCID 67958819, compound

HRID 2174665Notes

Reaction equation

HRID 2174665 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(CC)CC.[Cl-].[CH2:33]([O:35][C:36](=[O:48])[CH:37]([OH:47])[CH:38]([NH3+:46])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH3:34].[N:49]1[N:50]([C:58]2[N:66]=[CH:65][CH:64]=[CH:63][C:59]=2[C:60](O)=[O:61])[CH:51]=[C:52]2[C:57]=1[CH:56]=[CH:55][CH:54]=[CH:53]2>ClCCl>[N:49]1[N:50]([C:58]2[N:66]=[CH:65][CH:64]=[CH:63][C:59]=2[C:60]([NH:46][CH:38]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:37]([OH:47])[C:36]([O:35][CH2:33][CH3:34])=[O:48])=[O:61])[CH:51]=[C:52]2[C:57]=1[CH:56]=[CH:55][CH:54]=[CH:53]2

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67958419HCID 67958419, compoundHCID 86644788HCID 86644788, compound

Product 1

HCID 67958819HCID 67958819, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (1.748 g, 4.60 mmol) and Et3N (1 ml, 7.17 mmol) were successively added to a suspension of 4-ethoxy-3-hydroxy-4-oxo-1-phenylbutan-2-aminium chloride (1.303 g, 5.02 mmol) and 2-(2H-indazol-2-yl)nicotinic acid (1 g, 4.18 mmol) in dichloromethane (75 ml) at 5° C., and the mixture was stirred for 5 minutes. A pH of 10 was adjusted by adding Et3N (750 μl, 5.41 mmol), stirring was continued for 1 hour at 5° C. and then overnight at room temperature. The reaction mixture was then concentrated under reduced pressure and poured into 100 ml of water. The precipitate formed was filtered off with suction and dried in vacuo to give 1.05 g of the title compound as an off-white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour at 5° C.
  3. customovernight
  4. customat room temperature
  5. concentrationThe reaction mixture was then concentrated under reduced pressure
  6. additionpoured into 100 ml of water
  7. customThe precipitate formed
  8. filtrationwas filtered off with suction
  9. customdried in vacuo

Sources & evidence

ORD record
ord-75170e64cb25456aaa451ac753a873b4
Source dataset
uspto-grants-2015_06
Patent number
US09062027B2

Reaction notes

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