Triethylamine → HCID 67958397, compound

HRID 2174667Notes

Reaction equation

HRID 2174667 reaction equation
CN(C(ON1N=NC2[CH:12]=[CH:13][CH:14]=[N:15]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[N:32]1[N:33]([C:41]2[N:62]=[CH:61][CH:60]=[CH:59][C:42]=2[C:43]([NH:45][CH:46]([CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:47]([OH:51])[C:48]([OH:50])=O)=[O:44])[CH:34]=[C:35]2[C:40]=1[CH:39]=[CH:38][CH:37]=[CH:36]2.C1(N)CC1>ClCCl>[CH:14]1([NH:15][C:48](=[O:50])[CH:47]([OH:51])[CH:46]([NH:45][C:43](=[O:44])[C:42]2[CH:59]=[CH:60][CH:61]=[N:62][C:41]=2[N:33]2[CH:34]=[C:35]3[C:40]([CH:39]=[CH:38][CH:37]=[CH:36]3)=[N:32]2)[CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67958233HCID 67958233, compound

Product 1

HCID 67958397HCID 67958397, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HATU (201 mg, 0.528 mmol) and Et3N (0.127 ml, 0.913 mmol) were successively added to a suspension of 3-[2-(2H-indazol-2-yl)nicotinamido]-2-hydroxy-4-phenylbutanoic acid (200 mg, 0.480 mmol) and cyclopropylamine (0.034 ml, 0.48 mmol) in dichloromethane (50 ml) at 5° C., and the mixture was stirred for 5 minutes. A pH of 10 was adjusted by adding Et3N (0.1 ml, 0.720 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 50 ml of water. The precipitate formed was filtered off with suction and dried in vacuo to give 136 mg of the title compound as a 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 50 ml of water
  7. customThe precipitate formed
  8. filtrationwas filtered off with suction
  9. customdried in vacuo

Sources & evidence

ORD record
ord-245beb6ccd054468853297fac48d7bdf
Source dataset
uspto-grants-2015_06
Patent number
US09062027B2

Reaction notes

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