Diisopropylethylamine → HCID 57650264, compound

HRID 2063467Notes

Reaction equation

HRID 2063467 reaction equation
Cl.[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:12]([C@H:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)=[N:11][N:10]=[C:9]2[CH3:18])=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:45][C:46]([F:58])([F:57])[C:47]1[CH:52]=[CH:51][C:50]([CH2:53][C:54](O)=[O:55])=[CH:49][CH:48]=1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:9]([CH3:18])=[N:10][N:11]=[C:12]2[C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:54](=[O:55])[CH2:53][C:50]2[CH:49]=[CH:48][C:47]([C:46]([F:57])([F:45])[F:58])=[CH:52][CH:51]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 688114841140496-10-1

Product 1

HCID 57650264HCID 57650264, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole hydrochloride (50 mg, 0.8 mmol) was dissolved in dichloromethane (2 ml). HATU (75 mg, 0.19 mmol), (α,α,α-trifluoro-p-tolyl)acetic acid (37 mg, 0.18 mmol) and N,N-diisopropylethylamine (0.078 ml, 0.45 mmol) were added while stirring. The reaction mixture was stirred for 12 h then evaporated to dryness. Residue was taken up in EtOAc (20 ml) and washed with saturated solutions of NaHCO3 and NaCl. Organics were dried (NaSO4), filtered and concentrated. Purification by HPLC (water/acetonitrile gradient, 20% to 100% acetonitrile with 0.1% TFA) afforded the desired product as a white amorphous solid (76.3 mg, 91%).

Workup

  1. stirringThe reaction mixture was stirred for 12 h
  2. customthen evaporated to dryness
  3. washwashed with saturated solutions of NaHCO3 and NaCl
  4. dry with materialOrganics were dried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by HPLC (water/acetonitrile gradient, 20% to 100% acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-0c3621c250314b97a2352a3a391b7484
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

Loading…