Triethylamine → HCID 90466853, compound

HRID 1753244Notes

Reaction equation

HRID 1753244 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:15]=[CH:14][N:13]=3)[CH:9]=[C:8]([C:25]([OH:27])=O)[C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.Cl.[F:54][CH2:55][CH2:56][NH2:57]>ClCCl>[F:54][CH2:55][CH2:56][NH:57][C:25]([C:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=[C:4]2[N:10]([CH2:11][C:12]2[C:17]([CH3:18])=[C:16]([O:19][CH2:20][C:21]([F:22])([F:24])[F:23])[CH:15]=[CH:14][N:13]=2)[CH:9]=1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 111923Propylphosphonic anhydrideHCID 117819062HCID 117819062, compound

Product 1

HCID 90466853HCID 90466853, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

See FIG. 21(a). 6-methyl-1-((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (111 mg, 0.29 mmol) was taken dichloromethane (10 mL). Triethyl amine (0.204 mL, 1.46 mmol) was added to get a clear solution. 1-Propanephosphonic acid cyclic anhydride (0.348 mL, 0.59 mmol) was added and stirred at RT for 5 minutes. Added 2-Fluoroethylamine hydrochloride (87 mg, 0.88 mmol) and stirred at RT for overnight. After the completion of the reaction, diluted the reaction mass with dichloromethane, washed with water, brine solution. The organic layer was separated, dried over sodium sulphate, evaporated to get the crude compound. The compound was purified by silica gel chromatography using methanol and dichloromethane as eluent. Yield-44.3%. ES+MS m/z: 425.2 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.24 (s, 3 H ) 2.39 (s, 3 H ) 3.66 (q, J=5.21 Hz, 1 H ) 3.75 (q, J=5.15 Hz, 1 H ) 4.49 (t, J=4.99 Hz, 1 H ) 4.65 (t, J=4.99 Hz, 1 H ) 4.90 (q, J=8.85 Hz, 2 H ) 5.63 (s, 2 H ) 7.07 (d, J=5.65 Hz, 1 H ) 7.76 (s, 1 H ) 8.11 (s, 1 H ) 8.17 (d, J=5.65 Hz, 1 H ) 8.34 (s, 1 H ) 8.88 (t, J=5.84 Hz, 1 H ).

Workup

  1. customto get a clear solution
  2. customAfter the completion of the reaction
  3. washwashed with water, brine solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-73b3338a9f2647b5ac2f520529a617ba
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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