Triethylamine → HCID 71582012, compound

HRID 1747169Notes

Reaction equation

HRID 1747169 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[C:14]3[CH:15]=[C:16]([N:19]4[CH2:24][CH2:23][NH:22][C@H:21]([CH3:25])[CH2:20]4)[CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH3:9])=[C:4]([F:26])[CH:3]=1.C(OC([N:34]1[CH2:38][CH2:37][CH2:36][C@@H:35]1[C:39](O)=[O:40])=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]2[C:14]3[CH:15]=[C:16]([N:19]4[CH2:24][CH2:23][N:22]([C:39]([C@H:35]5[CH2:36][CH2:37][CH2:38][NH:34]5)=[O:40])[C@H:21]([CH3:25])[CH2:20]4)[CH:17]=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH3:9])=[C:4]([F:26])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86688437HCID 86688437, compound

Product 1

HCID 71582012HCID 71582012, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-((R)-1-(4-chloro-2-fluorophenyl)ethyl)-6-((R)-3-methylpiperazin-1-yl)-1H-benzo[d]imidazole (0.044 g, 0.11 mmol) and (R)-1-(t-butoxycarbonyl)pyrrolidine-2-carboxylic acid (0.047 g, 0.22 mmol) in dichloromethane (1 mL) was added HATU (0.084 g, 0.22 mmol) and Et3N (0.10 mL, 0.72 mmol). The reaction mixture was stirred at room temperature for 2 h, and diluted with ethyl acetate. The mixture was washed with deionized water, and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 50% ethyl acetate in hexanes) to afford the desired product (0.018 g, 0.031 mmol, 28%).

Workup

  1. washThe mixture was washed with deionized water
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (SiO2, 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e7353f9045024418a2793ce59cec08da
Source dataset
uspto-grants-2015_10
Patent number
US09150550B2

Reaction notes

Loading…