Triethylamine → HCID 90467010, compound

HRID 1753249Notes

Reaction equation

HRID 1753249 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]=[CH:16][CH:17]=3)[C:12]([NH2:19])=[CH:11]2)[C:4]=1[CH3:20].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[CH:46]1([CH2:49][C:50](O)=[O:51])[CH2:48][CH2:47]1>ClCCl.O>[CH:46]1([CH2:49][C:50]([NH:19][C:12]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:18]3[N:10]([CH2:9][C:5]3[C:4]([CH3:20])=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=3)[CH:11]=2)=[O:51])[CH2:48][CH2:47]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 138440Cyclopropaneacetic acidHCID 117818947HCID 117818947, compound

Product 1

HCID 90467010HCID 90467010, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-amine (25d) (0.1 g, 0.37 mmol) in dichloromethane (10 mL) were added triethylamine (0.15 mL, 1.11 mmol), T3P (0.35 g, 1.11 mmol) and 2-cyclopropylacetic acid (0.037 g, 0.37 mmol and the mixture was stirred for 16 h at room temperature. Then the reaction mixture was poured into water (20 mL) and extracted with dichloromethane (2×50 mL). The combined organic layer was washed with brine and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using 50% ethylacetate in hexane to afford 2-cyclopropyl-N-(1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)acetamide as off-white solid; yield: 25 mg (19%). ES+MS m/z: 352 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.25 (s, 3H), 3.67-3.69 (m, 1H), 3.73-3.76 (m, 1H), 4.50-4.52 (m, 1H), 4.62-4.64 (m, 1H), 5.49 (s, 2H), 6.94-6.96 (m, 3H), 7.27-7.30 (m, 1H), 8.08 (d, J=8.2 Hz), 8.45 (s, 1H), 8.50 (d, J=3.88 Hz), 8.92 (t, J=5.6 Hz).

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. washThe combined organic layer was washed with brine
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-659637cd2f194c05bfc539f84474b061
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

Loading…