Triethylamine → HCID 72792698, compound

HRID 1753253Notes

Reaction equation

HRID 1753253 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[C:12]([C:20](O)=[O:21])=[CH:11]2)[C:4]=1[CH3:23].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.Cl.[F:51][CH2:52][CH2:53][NH2:54]>C(Cl)Cl>[CH3:24][N:2]([CH3:1])[C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=3)[C:12]([C:20]([NH:54][CH2:53][CH2:52][F:51])=[O:21])=[CH:11]2)[C:4]=1[CH3:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 111923Propylphosphonic anhydrideHCID 117818455HCID 117818455, compound

Product 1

HCID 72792698HCID 72792698, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

See FIG. 23(d). 1-((6-(dimethylamino)-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (75 mg, 0.23 mmol) was taken in a thermal reactor. DCM (5 mL) was added to get a suspension. Triethyl amine (0.064 mL, 0.46 mmol) was added followed by the addition of 1-Propanephosphonic acid cyclic anhydride (0.274 mL, 0.46 mmol). 2-fluoroethanamine hydrochloride (22.94 mg, 0.23 mmol) was added and stirred at RT for ON. After the completion of the reaction, reaction mixture was concentrated and dissolved in DCM:MeOH. This crude compound was subjected for reverse phase purification. The final compound obtained 1-((6-(dimethylamino)-5-methylpyrimidin-4-yl)methyl)-N-(2-fluoroethyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (12.00 mg, 14.05%) as a white solid. ES+MS m/z: 371 (M+). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 3 H ) 2.40 (s, 3 H ) 2.95 (s, 6 H ) 3.66 (d, J=5.46 Hz, 1 H ) 3.75 (d, J=5.27 Hz, 1 H ) 4.49 (t, J=4.99 Hz, 1 H ) 4.65 (t, J=4.99 Hz, 1 H ) 5.54 (s, 2 H ) 7.75 (s, 1 H ) 8.13 (s, 1 H ) 8.22 (s, 1 H ) 8.34 (s, 1 H ) 8.88 (t, J=5.84 Hz, 1 H).

Workup

  1. customto get a suspension
  2. customAfter the completion of the reaction, reaction mixture
  3. concentrationwas concentrated
  4. dissolutiondissolved in DCM
  5. customThis crude compound was subjected for reverse phase purification

Sources & evidence

ORD record
ord-caa549508b5b40688549751a65308c59
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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