Triethylamine → HCID 90466854, compound

HRID 1753245Notes

Reaction equation

HRID 1753245 reaction equation
[CH3:1][O:2][C:3]1[C:8]([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)=[CH:7][C:6]([C:23]([F:26])([F:25])[F:24])=[CH:5][N:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[F:52][C@@H:53]([CH3:56])[CH2:54][NH2:55].C(N(CC)CC)C>CN1C(=O)CCC1.O>[F:52][C@@H:53]([CH3:56])[CH2:54][NH:55][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:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([C:23]([F:24])([F:25])[F:26])[CH:7]=2)[CH:11]=1)=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117819034HCID 117819034, compoundHCID 117819036HCID 117819036, compound

Product 1

HCID 90466854HCID 90466854, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

See FIG. 21(b). In a 25 mL thermal vial was charged with 1-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (100 mg, 0.27 mmol) and HATU (125 mg, 0.33 mmol) were taken in NMP (4 mL) and stirred for 10 min at rt. Then (S)-2-fluoropropan-1-amine hydrochloride (37.3 mg. 0.33 mmol) and triethyl amine (0.114 mL, 0.82 mmol) were added and stirred for 1 h at RT. The LCMS showed completion of the reaction. The reaction mixture was poured into water and extracted with chloroform. The organic layer was dried and concentrated and crude was submitted to reverse phase purification. The pure fractions were concentrated to get (S)—N-(2-fluoropropyl)-1-((2-methoxy-5-(trifluoromethyl)pyridin-3-yl)methyl)-6-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (82 mg, 70.6%) a solid. ES+MS m/z: 425 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.15-1.44 (m, 3 H ) 2.44 (s, 3 H ) 3.39-3.79 (m, 2 H ) 3.98 (s, 3 H ) 4.75 (td, J=6.50, 3.39 Hz, 1 H ) 4.92 (td, J=6.50, 3.20 Hz, 1 H ) 5.48 (s, 2 H ) 7.81 (d, J=2.26 Hz, 1 H ) 7.91-8.03 (m, 1H) 8.25 (s, 1 H ) 8.34-8.42 (m, 1 H ) 8.53-8.62 (m, 1 H ) 8.90 (t, J=5.93 Hz, 1 H ).

Workup

  1. stirringstirred for 1 h at RT
  2. customcompletion of the reaction
  3. extractionextracted with chloroform
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customphase purification
  7. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-e3a91ee420eb41a386b7c76ab68562dd
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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