Nitrogen → (S)-1-(2-methoxy-1-phenylethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

HRID 571424Notes

Reaction equation

HRID 571424 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[CH3:36][O:37][CH2:38][C@@H:39]([NH:46][C:47]([NH2:49])=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N#N>CC(N(C)C)=O>[CH3:36][O:37][CH2:38][C@@H:39]([NH:46][C:47]([NH:49][C:2]1[N:7]=[CH:6][C:5]2[C:8]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1)=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 89524417(S)-1-(2-methoxy-1-phenylethyl)ureaHCID 895258536-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 89525815(S)-1-(2-methoxy-1-phenylethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)ureaYield 100%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a vial were added 6-chloro-3-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine (47.6 mg, 0.100 mmol), (S)-1-(2-methoxy-1-phenylethyl)urea (38.8 mg, 0.200 mmol), cesium carbonate (0.024 ml, 0.300 mmol), CHLORO[2-(DICYCLOHEXYLPHOSPHINO)-3,6-DIMETHOXY-2′,4′,6′-TRI-I-PROPYL-1,1′-BIPHENYL][2-(2-AMINOETHYL)PHENYL]PALLADIUM(II) (15.98 mg, 0.020 mmol) and DMA (1.0 ml). The mixture was Vac/N2 purged 6 times and heated at 100° C. for 2 h. LC-MS showed complete conversion. The mixture was diluted with EtOAc and washed with water and brine. After dried over Na2SO4 the solution was concentrated to yield (S)-1-(2-methoxy-1-phenylethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (63.4 mg, 0.100 mmol, 100% yield) without purification.

Workup

  1. custompurged 6 times
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialAfter dried over Na2SO4 the solution
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-162de3cc006044ee9a2ef4929e885cc4
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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