Dimethylformamide → HCID 18332660, compound

HRID 2268950Notes

Reaction equation

HRID 2268950 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[CH2:20]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32](CN)[CH2:31]1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:37][N:38](C=O)C>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:20]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32]([N:38]([CH3:37])[C:5]2[N:10]=[C:9]([N:11]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[N:13]=[CH:12]3)[CH:8]=[CH:7][N:6]=2)[CH2:31]1)=[O:29])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 155496402-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidineHCID 15550581Benzyl 3-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 18332660HCID 18332660, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 336 mg of 2-methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 1) in 2 mL of DMF was added a solution of 273 mg of 1-benzyloxycarbonyl-3-aminomethylpyrrolidine in 2 mL of toluene. The mixture was heated to 100° C. and stirred at this temperature for 18 h, then cooled, diluted with 20 mL of EtOAc, and washed with 2×10 mL of water and 10 ml of brine. The organic phase was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with a gradient system of 4:1 hexanes-acetone to 2:1 hexanes-acetone, to yield 338 mg of the title compound as an off-white foam. 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H), 8.38 (d, J=5.0 Hz, 1H) 8.16 (br t, J=7.1 Hz, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.27-7.42 (m, 5H), 6.81 (d, J=5.5 Hz, 1H), 5.55 (br s, 1H), 5.06-5.19(m, 2H), 3.50-3.75 (m, 4H), 3.38-3.50 (m, 1H), 3.25 (ddd, J=6.9, 10.8, 17.6 Hz, 1H), 2.58-2.70 (m, 1H), 2.06-2.16 (m, 1H), 1.68-1.82 (m, 1H). Mass spectrum (ESI) 429.2 (M+1).

Workup

  1. temperaturecooled
  2. washwashed with 2×10 mL of water and 10 ml of brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with a gradient system of 4:1 hexanes-acetone to 2:1 hexanes-acetone

Sources & evidence

ORD record
ord-5c13fcab9da04ba5ba2ed8ad1f00ec92
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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