Triethylamine → (S)-2-[6-chloro-5-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-pyrimidin-4-ylamino]-3-phenyl-propan-1-ol

HRID 1354641Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([N:18]4[CH:22]=[CH:21][N:20]=[CH:19]4)[CH:15]=[C:16]([CH3:17])[C:10]=3[N:9]=2)=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH2:24][C@@H:25]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:26][OH:27].C(N(CC)CC)C>C(O)(C)C>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([NH:24][C@@H:25]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:26][OH:27])[C:7]=1[C:8]1[NH:12][C:11]2[CH:13]=[C:14]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)[CH:15]=[C:16]([CH3:17])[C:10]=2[N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(4,6-dichloro-pyrimidin-5-yl)-6-imidazol-1-yl-4-methyl-1H-benzimidazole (40 mg, 0.16 mmol) in isopropanol (5 mL) was added (S)-(−)-2-amino-3-phenyl-propanol (35 mg, 0.23 mmol) and triethylamine (0.5 mL). The reaction mixture was heated to 80° C. for 4 h, cooled to room temperature and concentrated with high vacuum. The crude product was used for the next step without purification. LCMS (M+H)+ m/z 460 (t=2.13 min.).

Workup

temperaturecooled to room temperature
concentrationconcentrated with high vacuum
customThe crude product was used for the next step without purification
customLCMS (M+H)+ m/z 460 (t=2.13 min.)

Sources & evidence

ORD record: ord-9bb735da41fb44ea9e8f91e8e7d38e0a
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223757B2

Reaction notes

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