Tetrahydrofuran → HCID 178514081, compound

HRID 1012152Notes

Reaction equation

HRID 1012152 reaction equation
[N:1]1([CH2:7][C:8]2[CH:22]=[CH:21][C:11]3[NH:12][C:13]([C:15]4[C:19]([NH2:20])=[CH:18][NH:17][N:16]=4)=[N:14][C:10]=3[CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N:23]1(C(Cl)=O)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.C([N:35]([CH:38](C)C)CC)(C)C.C1C[O:44]CC1>>[N:23]1([N:20]([C:19]2[C:15]([C:13]3[NH:12][C:11]4[CH:21]=[CH:22][C:8]([CH2:7][N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:9][C:10]=4[N:14]=3)=[N:16][NH:17][CH:18]=2)[C:38]([NH2:35])=[O:44])[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 178508054HCID 178508054, compound

Product 1

HCID 178514081HCID 178514081, compound

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (70 mg, 0.23 mmol), morpholine-4-carbonyl chloride (80 μl, 0.7 mmol) and diisopropylethylamine (170 μl, 0.92 mmol) in THF (2 ml) was stirred at 0° C. and then allowed to warm to room temperature over 16 h. The reaction was quenched by the addition of conc. aq. NH3 and then concentrated in vacuo. The residue was purified through preparative LC/MS to give 4-morpholinyl-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1-H-pyrazol-4-yl]-urea as a white solid (35 mg). (LC/MS (basic method): Rt 2.28 min, [M−H+]− 415).

Workup

  1. temperatureto warm to room temperature over 16 h
  2. customThe reaction was quenched by the addition of conc. aq. NH3
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified through preparative LC/MS

Sources & evidence

ORD record
ord-8d3218cd670041bbaf3f9ccfd9d12573
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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