Triethylamine → HCID 90467013, compound

HRID 1753254Notes

Reaction equation

HRID 1753254 reaction equation
[CH3:1][O:2][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]([OH:22])=O)=[CH:11]2)[C:4]=1[CH3:23].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[F:49][CH:50]([F:53])[CH2:51][NH2:52]>C(Cl)Cl>[F:49][CH:50]([F:53])[CH2:51][NH:52][C:20]([C:12]1[C:13]2=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=[C:18]2[N:10]([CH2:9][C:5]2[C:4]([CH3:23])=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=2)[CH:11]=1)=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 1362742,2-DifluoroethanamineHCID 117819025HCID 117819025, compound

Product 1

HCID 90467013HCID 90467013, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

See FIG. 24(a). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (100 mg, 0.32 mmol) was taken in a thermal reactor. DCM (3 mL) was added to get a suspension. Triethyl amine (0.089 mL, 0.64 mmol) was added followed by the addition of 1-Propanephosphonic acid cyclic anhydride (0.381 mL, 0.64 mmol). 2,2-difluoroethanamine (26.0 mg, 0.32 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 to obtain N-(2,2-difluoroethyl)-1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (20.00 mg, 16.64%) as a off white solid. ES+MS m/z: 376 (M−1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.24 (s, 4 H ) 2.40 (s, 3 H ) 3.77-3.89 (m, 2 H ) 3.93 (s, 4 H) 5.65 (s, 2 H ) 7.77 (s, 1 H ) 8.20 (s, 1 H ) 8.40 (s, 1 H ) 8.36 (s, 1 H ) 8.91 (br. s., 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-c59423a856a34b549e19cfeecc7a9d8d
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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