3-Aminopyridine → HCID 58279317, compound

HRID 85109Notes

Reaction equation

HRID 85109 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][CH:20]=[C:21]([C:22](O)=[O:23])[C:15]=4[N:14]=3)=[C:9]([C:25]([F:28])([F:27])[F:26])[CH:8]=2)[CH2:3][CH2:2]1.CN(C(ON1N=[N:44][C:39]2[CH:40]=[CH:41][CH:42]=[N:43][C:38]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.NC1C=NC=CC=1>CN(C=O)C.O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:17][C:16]4[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([NH:44][C:39]5[CH:38]=[N:43][CH:42]=[CH:41][CH:40]=5)=[O:23])[C:15]=4[N:14]=3)=[C:9]([C:25]([F:27])([F:26])[F:28])[CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67202695HCID 67202695, compound

Product 1

HCID 58279317HCID 58279317, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-morpholino-2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (20; 157 mg, 0.40 mmol), HATU (304 mg, 0.80 mmol), DIEA (207 mg, 1.60 mmol) and 3-aminopyridine (173; 37 mg, 0.40 mmol) in DMF (2 mL) was stirred at room temperature for 12 h. Water (20 mL) was added and stirred for 30 min. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to give 2-(4-morpholino-2-(trifluoromethyl)phenyl)-N-(pyridin-3-yl)-1H-benzo[d]imidazole-4-carboxamide (Compound 430) (64 mg, 34%) as a pale yellow solid. MS (ESI) calcd for C24H20F3N5O2: 467.16; found: 468 [M+H].

Workup

  1. stirringstirred for 30 min
  2. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography

Sources & evidence

ORD record
ord-dbf55ac9d87042fd9bf68774efbd6b53
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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