Triethylamine → HCID 178433096, compound

HRID 457564Notes

Reaction equation

HRID 457564 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([C:23]4[C:24](=[O:30])[NH:25][CH:26]=[CH:27][C:28]=4Cl)[NH:20]3)=[C:16]([CH3:31])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:40][CH2:41][C@H:42]([C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([Cl:50])[CH:45]=1)[OH:43]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([C:23]4[C:24](=[O:30])[NH:25][CH:26]=[CH:27][C:28]=4[NH:40][CH2:41][C@H:42]([C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([Cl:50])[CH:45]=4)[OH:43])[NH:20]3)=[C:16]([CH3:31])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11550227(S)-2-AMINO-1-(3-CHLOROPHENYL)ETHANOL HYDROCHLORIDEHCID 178433095HCID 178433095, compound

Product 1

HCID 178433096HCID 178433096, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[8-(4-chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-6-methyl-9H-purin-2-yl]-piperazine-1-carboxylic acid t-butyl ester (200 mg, 0.448 mmol) in acetonitrile (10 mL) was added triethylamine (125 μl, 0.896 mmol) and (S)-2-amino-1-(3-chlorophenyl)-ethanol hydrochloride (99 mg, 0.493 mmol). The reaction mixture was stirred at 80° C. for 18 hours in a sealed tube and concentrated. The residue was dissolved in CH2Cl2 (50 mL) washed with H2O (2×30 mL), dried over MgSO4 and concentrated. The crude material was purified by crystallization in hot MeOH (35 mL) to give the title compound as a beige solid. (0.197 g, 76%). HPLC 98%; LCMS (+ESI, M+H+) m/z 581; IR (KBr, cm−1) 3419, 3271, 2975, 1696, 1496, 1232; 1H NMR (400 MHz, DMSO+D2O) δ 10.79 (br s, 1H), 7.59–7.32 (m, 5H), 6.22 (d, J=7.6 Hz, 1H), 5.00 (br t, 1H), 3.73 (br s, 4H, 3.60 (m, 1H), 3.44 (br s, 4H), 2.58 (s, 3H); HRMS calcd for C28H33ClN8O4: 581.2391; found 581.2389.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  3. washwashed with H2O (2×30 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by crystallization in hot MeOH (35 mL)

Sources & evidence

ORD record
ord-5b75637952bb42bab7410f635909a095
Source dataset
uspto-grants-2007_03
Patent number
US07189716B2

Reaction notes

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