Ethanolamine → US9777003, Example 210

HRID 628435Notes

Reaction equation

HRID 628435 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14](Cl)[C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([CH2:25][NH2:26])[OH:24].C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1.O.CC#N.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.CS([O-])(=O)=O.C1C=[C-]C(C2C(N)=CC=CC=2)=CC=1.[Pd+2]>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([NH:26][CH2:25][CH2:23][OH:24])[C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 700EthanolamineHCID 10796Cesium carbonateHCID 1181596216-benzyl-4-chloro-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 118159716US9777003, Example 210

Reagents, catalysts & solvents 4

HCID 86346478Ditert-butyl-[3,6-dimethoxy-2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane;methanesulfonate;palladium(2+);2-phenylanilineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A degassed mixture of 6-benzyl-4-chloro-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (25.0 mg, 0.0804 mmol, Example 228, Step 7), ethanolamine (44 mg, 0.72 mmol, Aldrich), Cs2CO3 (79 mg, 0.24 mmol, Aldrich) and tBuBrettPhos Pd G3 (8.2 mg, 0.0096 mmol, Aldrich) in NMP (1 mL) and Water (38 μL) was heated at 100° C. overnight. Upon cooling, the reaction mixture was diluted with MeCN, filtered and purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (5.9 mg, 22%).

Workup

  1. temperatureUpon cooling
  2. filtrationfiltered
  3. custompurified via preparative HPLC-MS (Waters XBridge C18
  4. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-ce660277387a47b598ff68abac6f41f6
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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