L-Proline → 5-[2-(5-Bromo-2-1,2,4-triazol-1-yl-phenyl)-1-tert-butyl-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

HRID 1966674Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[Br:20][C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH:33]=[N:32][CH:31]=[N:30]2)=[C:25]([CH:28]=1)[CH:26]=O.N1CCC[C@H]1C(O)=O>CO>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([N:29]2[CH:33]=[N:32][CH:31]=[N:30]2)=[C:25]([C:26]2[N:14]([C:15]([CH3:16])([CH3:18])[CH3:17])[C:11]3[CH:12]=[CH:13][C:8]([C:5]4[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=4)=[CH:9][C:10]=3[N:19]=2)[CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (100 mg, 0.39 mmol) in MeOH (5 mL) are added 5-bromo-2-1,2,4-triazol-1-yl-benzaldehyde (refer to example 4 step 1) (147 mg, 0.58 mmol) and L-proline (4 mg, 0.04 mmol) at room temperature. The solution is heated to 60° C. for 24 hours and then cooled down and is concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the title compound (59 mg, 31%) as a white foam. LCMS (ESMS): m/z 489.20 (M+)

Workup

temperaturecooled down
concentrationis concentrated under reduced pressure
customThe residue is purified by silica gel flash column chromatography
washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record: ord-7f9e07f1c441499aa6349c12dead3af7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420655B2

Reaction notes

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