Triethylamine → HCID 75204200, compound

HRID 1755239Notes

Reaction equation

HRID 1755239 reaction equation
[C:1]1([N:7]2[CH:11]=[N:10][C:9]([C:12]([OH:14])=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:15]1[N:19]2[CH:20]=[CH:21][N:22]=[C:23]([N:24]3[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25]3)[C:18]2=[CH:17][CH:16]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CS(C)=O>[C:1]1([N:7]2[CH:11]=[N:10][C:9]([C:12]([NH:29][C@H:26]3[CH2:27][CH2:28][N:24]([C:23]4[C:18]5[N:19]([N:15]=[CH:16][CH:17]=5)[CH:20]=[CH:21][N:22]=4)[CH2:25]3)=[O:14])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 123160561-Phenyl-1H-1,2,4-triazole-3-carboxylic acidHCID 75204199(S)-1-(pyrazolo[1,5-a]pyrazin-4-yl)pyrrolidin-3-amine

Product 1

HCID 75204200HCID 75204200, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-phenyl-1H-1,2,4-triazole-3-carboxylic acid (0.093 g, 0.49 mmol, 1.4 eq) and (S)-1-(pyrazolo[1,5-a]pyrazin-4-yl)pyrrolidin-3-amine (0.10 g, 0.36 mmol, 1 eq) in 1 mL of DMSO was added triethylamine (0.20 mL, 1.4 mmol, 2.6 eq) and HATU (0.21 g, 0.55 mmol, 1.5 eq). After stirring for 1 h at room temperature, the mixture was concentrated and purified by HPLC to afford (S)-1-phenyl-N-(1-(pyrazolo[1,5-a]pyrazin-4-yl)pyrrolidin-3-yl)-1H-1,2,4-triazole-3-carboxamide (0.095 g, 0.25 mmol, 52%). 1H NMR (400 MHz, CD3OD) δ 9.13 (s, 1 H), 8.16 (d, J=2.4 Hz, 1 H), 8.09 (d, J=5.8 Hz, 1 H), 7.86 (d, J=7.8 Hz, 2 H), 7.60-7.46 (m, 4 H), 7.19 (d, J=5.5 Hz, 1 H), 4.95-4.80 (m, 1 H), 4.78-3.80 (br, 4 H), 2.62-2.40 (m, 2 H); MS: (ES) m/z calculated for C19H18N8O [M+H]+ 375.2, found 375.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-92eac95bde5d40a7b135590523ba5e76
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

Loading…