1,2-Dichloroethane → N-(2-Aminophenyl)-1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidine-3-carboxamide

HRID 2202826Notes

Reaction equation

[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([N:15]3[CH2:18][CH:17]([C:19]([OH:21])=O)[CH2:16]3)[CH:9]=2)[N:3]=1.[C:22]1([NH2:29])[C:23]([NH2:28])=[CH:24][CH:25]=[CH:26][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:29][C:19]([CH:17]1[CH2:16][N:15]([C:10]2[CH:9]=[C:8]([N:4]3[C:5]([CH3:7])=[N:6][C:2]([CH3:1])=[N:3]3)[N:13]=[C:12]([CH3:14])[N:11]=2)[CH2:18]1)=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 107-2 (584 mg, 2.03 mmol), benzene-1,2-diamine (263 mg, 2.43 mmol), HOBt (465 mg, 3.04 mmol), EDC (582 mg, 3.04 mmol) and DIEA (1.77 mL, 10.1 mmol) were combined in degassed DMF (10 mL) and heated at 50° C. for 18 h. The mixture was cooled to room temperature, poured into sodium bicarbonate (200 mL, aqueous saturated) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-100% EtOAc (containing 10% MeOH)/hexanes), providing 107-3 as a pale green solid. MS: m/z=379.3 (M+H).

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate (2×100 mL)
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (0-100% EtOAc (containing 10% MeOH)/hexanes)

Sources & evidence

ORD record: ord-54a19e056e72414283bace0a3ea088d2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365562B2

Reaction notes

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