Triethylamine → HCID 72792836, compound

HRID 1753255Notes

Reaction equation

HRID 1753255 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([OH:16])=O)=[CH:6]1.C(N(CC)CC)C.CCCP(O)(O)=O.Cl.[F:37][CH2:38][CH2:39][NH2:40]>C(Cl)Cl>[CH3:1][C:2]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([NH:40][CH2:39][CH2:38][F:37])=[O:16])=[CH:6]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 204484Propylphosphonic acidHCID 117818753HCID 117818753, compound

Product 1

HCID 72792836HCID 72792836, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

See FIG. 24(b). 1-(2,4-dimethylbenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (200 mg, 0.71 mmol) was taken in a 100 ml single necked flask equipped with an air condenser connected to nitrogen source. Added CH2Cl2 (10 mL) to get a clear solution. Triethylamine (5 mL, 35.87 mmol) was added followed by the addition of 1-Propylphosphonic acid cyclic anhydride (2 mL, 1.43 mmol) and 2-Fluoroethylamine hydrochloride (142 mg, 1.43 mmol). The reaction mass was stirred at RT for overnight. This crude compound was subjected for reverse phase purification to obtain 1-(2,4-dimethylbenzyl)-N-(2-fluoroethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (50.00 mg, 22%) as a off white solid. ES+MS m/z: 326 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.21 (s, 3 H ) 2.24 (s, 3 H ) 3.57-3.86 (m, 2 H ) 4.50 (t, J=4.99 Hz, 1 H ) 4.66 (t, J=4.99 Hz, 1 H ) 5.41-5.60 (m, 2 H ) 6.72 (d, J=7.72 Hz, 1 H ) 6.94 (d, J=7.54 Hz, 1 H ) 7.05 (s, 1 H ) 7.28 (dd, J=8.29, 4.71 Hz, 1 H ) 7.98 (dd, J=8.38, 1.04 Hz, 1 H ) 8.13 (s, 1 H ) 8.51 (dd, J=4.62, 1.04 Hz, 1 H ) 8.94 (t, J=5.84 Hz, 1 H ).

Workup

  1. customequipped with an air condenser
  2. customThis crude compound was subjected for reverse phase purification

Sources & evidence

ORD record
ord-d3fa7480d08043f1944d3f67e61d977a
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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