Triethylamine → HCID 90466705, compound

HRID 1753236Notes

Reaction equation

HRID 1753236 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][N:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24](O)=[O:25])=[CH:16]2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(OCC)(=O)C.Cl.[F:59][CH2:60][CH2:61][NH2:62]>C(Cl)Cl>[F:59][CH2:60][CH2:61][NH:62][C:24]([C:17]1[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:23]2[N:15]([CH2:14][C:3]2[C:2]([CH3:1])=[C:7]([O:8][CH2:9][C:10]([F:12])([F:11])[F:13])[CH:6]=[CH:5][N:4]=2)[CH:16]=1)=[O:25]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 111923Propylphosphonic anhydrideHCID 117819063HCID 117819063, compound

Product 1

HCID 90466705HCID 90466705, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

See FIG. 18(d). 1-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (100 mg, 0.27 mmol) was taken in DCM (10 mL) to get a clear solution. Triethyl amine (0.190 mL, 1.37 mmol) was added followed by the addition of 1-Propanephosphonic acid cyclic anhydride solution in ethyl acetate (0.326 mL, 0.55 mmol) and stirred the reaction mass for 5 minutes. 2-Fluoroethylamine hydrochloride (54.5 mg, 0.55 mmol) was added and stirred the reaction mass for 3 h. After completion of the reaction, diluted with DCM and then washed with water and brine solution. The organic layer was separated, dried, evaporated and the crude compound was purified by silica gel chromatography using methanol and dichloromethane as eluent. Yield-49%. ES+MS m/z: 411 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.25 (s, 3 H ) 3.67 (q, J=5.21 Hz, 1 H ) 3.76 (q, J=5.21 Hz, 1 H ) 4.50 (t, J=4.99 Hz, 1 H ) 4.66 (t, J=4.90 Hz, 1 H ) 4.90 (q, J=8.85 Hz, 2 H ) 5.68 (s, 2 H ) 7.06 (d, J=5.84 Hz, 1 H ) 7.24 (dd, J=8.38, 4.62 Hz, 1 H ) 7.93 (d, J=7.35 Hz, 1 H ) 8.17 (d, J=5.65 Hz, 1 H ) 8.24 (s, 1 H ) 8.48 (d, J=3.77 Hz, 1 H ) 8.94 (t, J=5.75 Hz, 1 H ).

Workup

  1. customto get a clear solution
  2. stirringstirred the reaction mass for 3 h
  3. customAfter completion of the reaction
  4. washwashed with water and brine solution
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated
  8. customthe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-36f820b6a4e84af79b85ad99e1a3374c
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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