Isopropylamine → Vimseltinib

HRID 709993Notes

Reaction equation

HRID 709993 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:5][N:4]=[C:3]1SC.[CH:31]([NH2:34])([CH3:33])[CH3:32]>>[CH:31]([NH:34][C:3]1[N:2]([CH3:1])[C:7](=[O:8])[C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]4[CH:23]=[N:24][N:25]([CH3:27])[CH:26]=4)[CH:17]=3)=[C:11]([CH3:28])[N:10]=2)=[CH:5][N:4]=1)([CH3:33])[CH3:32]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 90416241HCID 90416241, compound

Product 1

HCID 86267612VimseltinibYield 61.8%

Procedure

A mixture of Example C3 (0.14 g, 0.33 mmol) and isopropyl amine (3 mL, 35.0 mmol) was heated at 100° C. for 2 days in a sealed tube. The mixture was cooled to RT, the solid removed via filtration and the filtrate concentrated to dryness and purified via silica gel chromatography to obtain 2-(isopropylamino)-3-methyl-5-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)pyrimidin-4(3H)-one (88 mg, 59%). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 8.28 (d, J=8.7 Hz, 1H), 8.25 (s, 1H), 7.96 (d, J=0.7 Hz, 1H), 7.52 (d, J=8.6 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 7.05 (d, J=7.6 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 4.33 (m, 1H), 3.85 (s, 3H), 3.37 (s, 3H), 2.35 (s, 3H), 1.23 (d, J=6.6 Hz, 6H); MS (ESI) m/z: 432.2 (M+H+).

Workup

  1. customthe solid removed via filtration
  2. concentrationthe filtrate concentrated to dryness
  3. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-6e41b28e08494403863226e630b35a86
Source dataset
uspto-grants-2015_11
Patent number
US09181223B2

Reaction notes

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