Water → HCID 58980004, compound

HRID 1821173Notes

Reaction equation

HRID 1821173 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5](C2C=CC(CN)=CC=2)=[N:4]1)[CH3:2].C([N:27]([CH2:30]C)[CH2:28][CH3:29])C.[C:32]1([N:38]=[C:39]=O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[OH2:41].O1[CH2:46][CH2:45][CH2:44][CH2:43]1>>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:35]2[CH:36]=[CH:37][C:32]([N:38]([CH3:39])[C:30]([NH:27][C:28]3[CH:29]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:41])=[CH:33][CH:34]=2)=[N:4]1)[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 7672Phenyl isocyanateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 69000342{4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}methylamine

Product 1

HCID 58980004HCID 58980004, compoundYield 42%

Procedure

A solution of {4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]phenyl}methylamine (0.16 mmol) in tetrahydrofuran (1 mL) was treated with triethylamine (0.17 mmol), and phenyl isocyanate (0.17 mmol). After stirring 18 h at room temperature the reaction was poured into water (1 mL), and extracted with (3×1 mL) ethyl acetate. The combined organic layers were washed with water (2×1 mL), brine (1×1 mL) dried over sodium sulfate and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC provided the title product as a white powder (42%). ESMS [M+H]+: 437.2

Workup

  1. extractionextracted with (3×1 mL) ethyl acetate
  2. washThe combined organic layers were washed with water (2×1 mL), brine (1×1 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-5f1313b4c62e4393a2b4a6a6ad553219
Source dataset
uspto-grants-2009_10
Patent number
US07605266B2

Reaction notes

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