N-(2-Aminophenyl)-1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidine-3-carboxamide → 2-(1-(6-(3,5-Dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1H-benzo[d]imidazole

HRID 2202827Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([CH:11]1[CH2:14][N:13]([C:15]2[CH:20]=[C:19]([N:21]3[C:25]([CH3:26])=[N:24][C:23]([CH3:27])=[N:22]3)[N:18]=[C:17]([CH3:28])[N:16]=2)[CH2:12]1)=O>C(O)(=O)C>[CH3:27][C:23]1[N:24]=[C:25]([CH3:26])[N:21]([C:19]2[N:18]=[C:17]([CH3:28])[N:16]=[C:15]([N:13]3[CH2:14][CH:11]([C:9]4[NH:8][C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[N:1]=4)[CH2:12]3)[CH:20]=2)[N:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Compound 107-3 (175 mg, 0.462 mmol) was dissolved in acetic acid (10 mL) and heated at 100° C. for 18 h. The mixture was cooled to room temperature, the solvent was removed in vacuo, and the residue was purified by silica gel chromatography (0-100% EtOAc (containing 10% MeOH)/hexanes), providing Example 107 as a light yellow solid. 1H NMR: (400 MHz, CDCl3) δ 9.93 (br s, 1H), 7.62-7.60 (m, 2H), 7.29-7.26 (m, 2H), 6.30 (s, 1H), 4.62-4.52 br m, 2H), 4.40-4.30 (br m, 3H), 2.84 (s, 3H), 2.50 (s, 3H), 2.34 (s, 3H) ppm; MS: m/z=361.3 (M+H).

Workup

temperatureThe mixture was cooled to room temperature
customthe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography (0-100% EtOAc (containing 10% MeOH)/hexanes)

Sources & evidence

ORD record: ord-9d45843c2e9b4cb2972061557def0702
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365562B2

Reaction notes

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