Triethylamine → HCID 72792697, compound

HRID 1753239Notes

Reaction equation

HRID 1753239 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][C@H:50]([CH3:53])[CH2:51][NH2:52]>ClCCl>[F:49][C@@H:50]([CH3:53])[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 117819025HCID 117819025, compoundHCID 129360493HCID 129360493, compound

Product 1

HCID 72792697HCID 72792697, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

See FIG. 19(d). 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 dichloromethane (10 mL) to get a suspension. Added triethyl amine (0.133 mL, 0.96 mmol) followed by the addition of 1-Propanephosphonic acid cyclic anhydride (0.381 mL, 0.64 mmol). The reaction mass was stirred at RT for 5 minutes. (R)-2-fluoropropan-1-amine (49.4 mg, 0.64 mmol) was added and stirred at RT for overnight. After the completion of the reaction, diluted the reaction mass with DCM, washed ith water, and brine solution. The organic layer was dried over sodium sulphate, evaporated and the crude compound was purified by silica gel chromatography. Yield-75%. ES+MS m/z: 373.2 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.25-1.42 (m, 4 H ) 2.24 (s, 3H) 2.40 (s, 3 H ) 3.42-3.81 (m, 2 H ) 3.94 (s, 3 H ) 4.65-4.85 (m, 1 H ) 4.93 (td, J=6.50, 3.39 Hz, 1 H ) 5.64 (s, 2 H ) 7.76 (s, 1 H ) 8.16 (s, 1 H ) 8.29-8.47 (m, 2 H ) 8.91 (t, J=6.03 Hz, 1 H ).

Workup

  1. customto get a suspension
  2. stirringstirred at RT for overnight
  3. customAfter the completion of the reaction
  4. washwashed ith water, and brine solution
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. customevaporated
  7. customthe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d0c5e3ffc7f643bda2bb56f763f9487f
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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