Isopropanol → HCID 178514080, compound

HRID 1012150Notes

Reaction equation

HRID 1012150 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.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1N=C=O.CC[N:36]([CH2:39]C)CC.CC([OH:44])C>C1(C)C=CC=CC=1.CCOC(C)=O>[F:23][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([F:30])[C:29]=1[N:20]([C:19]1[C:15]([C:13]2[NH:12][C:11]3[CH:21]=[CH:22][C:8]([CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:9][C:10]=3[N:14]=2)=[N:16][NH:17][CH:18]=1)[C:39]([NH2:36])=[O:44]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 5932582,4-Difluorophenyl isocyanateHCID 178508054HCID 178508054, compound

Product 1

HCID 178514080HCID 178514080, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (50 mg, 0.16 mmol), 2,4 difluorophenyl isocyanate (26 mg, 0.16 mmol) and Et3N (0.024 ml) suspended in a mixture of toluene (2 ml) and IPA (1 ml) was stirred at 80° C. for 1 h and then diluted with EtOAc. The reaction mixture was washed with water then brine, organics dried (MgSO4) and reduced in vacuo The residue was purified by flash column chromatography [SiO2, CH2Cl2-MeOH (90:10)] to give 1-(2,6-Difluorophenyl)-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-urea (AT7787) as a colourless solid (30 mg, 39%). (LC/MS (acidic method): Rt 1.80, [M+H]+ 454).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialbrine, organics dried (MgSO4)
  3. customwas purified by flash column chromatography [SiO2, CH2Cl2-MeOH (90:10)]

Sources & evidence

ORD record
ord-97f7c4db7fed4efeadb47fa23f950230
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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