Triethylamine → HCID 67959705, compound

HRID 1529297Notes

Reaction equation

HRID 1529297 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=4[F:24])[CH:15]=3)[N:10](C(OC(C)(C)C)=O)[CH:9]=2)[CH:5]=[N:4][CH:3]=1.CC[N:34]([CH2:37][CH3:38])[CH2:35][CH3:36].[CH3:39][N:40]1C(=O)CCC1>C(Cl)Cl.O>[F:23][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([F:24])[C:17]=1[C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:6]1[N:7]=[C:2]([N:34]2[CH2:35][CH2:36][CH:39]([NH2:40])[CH2:38][CH2:37]2)[CH:3]=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 86709767HCID 86709767, compound

Product 1

HCID 67959705HCID 67959705, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A glass microwave reaction vessel was charged with tert-butyl 3-(6-chloropyrazin-2-yl)-5-(2,6-difluorophenyl)-1H-indole-1-carboxylate (50.0 mg, 0.113 mmol) and 4-boc-amino-1-piperidine (34.0 mg, 0.170 mmol) in NMP (0.6 mL), followed by Et3N (0.047 mL, 0.339 mmol). The reaction mixture was stirred and heated in an oil bath at 150° C. for 16 h, and then the mixture was diluted with DCM and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was dissolved in DCM (2 mL) and treated with TFA (0.5 mL). The reaction mixture was stirred at RT for 2 h, and solvent was removed. The residue was purified with RP-HPLC to give 1-(6-(5-(2,6-difluorophenyl)-1H-indol-3-yl)pyrazin-2-yl)piperidin-4-amine as a brown solid. MS (ESI, pos. ion) m/z: 406 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DCM (2 mL)
  7. additiontreated with TFA (0.5 mL)
  8. stirringThe reaction mixture was stirred at RT for 2 h
  9. customsolvent was removed
  10. customThe residue was purified with RP-HPLC

Sources & evidence

ORD record
ord-c19067c2b6d1447bb7a65f73b4e59bad
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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