Triethylamine → HCID 69426236, compound

HRID 970360Notes

Reaction equation

HRID 970360 reaction equation
Cl[C:2]1[C:7]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH:15]=[C:16]([CH3:17])[C:10]=3[N:9]=2)=[C:6]([O:24][CH3:25])[N:5]=[C:4]([O:26][CH3:27])[N:3]=1.C(N(CC)CC)C.Cl.[NH2:36][CH2:37][C@H:38]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([Cl:46])[CH:41]=1)[OH:39]>C(#N)C>[Cl:46][C:42]1[CH:41]=[C:40]([CH:38]([OH:39])[CH2:37][NH:36][C:2]2[C:7]([C:8]3[NH:12][C:11]4[CH:13]=[C:14]([N:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[CH:15]=[C:16]([CH3:17])[C:10]=4[N:9]=3)=[C:6]([O:24][CH3:25])[N:5]=[C:4]([O:26][CH3:27])[N:3]=2)[CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11550227(S)-2-AMINO-1-(3-CHLOROPHENYL)ETHANOL HYDROCHLORIDEHCID 59020270HCID 59020270, compound

Product 1

HCID 69426236HCID 69426236, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-chloro-2,6-dimethoxy-pyrimidin-5-yl)-4-methyl-6-morpholin-4-yl-1H-benzoimidazole (0.075 g, 0.192 mmol) in acetonitrile (5 mL) was added triethylamine (134 μl, 0.962 mmol) and (S)-2-Amino-1-(3-chloro-phenyl)-ethanol hydrochloride (42 mg, 0.202 mmol). The crude material was purified on silicagel dry colomn using AcOEt: Hex (8:2) to give the title compound as a beige solid. (0.055 g, 55%). HPLC 98%. LCMS 20 (+ESI, M+H+) m/z 525. IR (KBr, cm−1) 3446, 2955, 1595, 1472, 1367. 1H NMR (400 MHz, DMSO) δ 11.63 (s, 1H), 11.1 (m, 1H), 7.54 (s, 1H), 7.41-7.28 (m, 3H), 6.87 (d, J=2.0 Hz, 1H), 6.78 (s, 1H) 5.85 (s. 1H), 4.88 (m, 1H), 4.05 (s, 3H), 3.91-3.84 (m, 4H), 3.79-3.77 (m, 4H), 3.73-3.69 (m, 1H), 3.09-3.07 (m, 4H), 2.50 (3H, s). HRMS calcd for C26H29ClN6O4:525.2017; found 525.2008.

Workup

  1. customThe crude material was purified on silicagel
  2. customdry colomn

Sources & evidence

ORD record
ord-4471d4cdd767485a8960ea367d5f2ea0
Source dataset
uspto-grants-2007_12
Patent number
US07312215B2

Reaction notes

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