Methylamine → HCID 72725461, compound

HRID 591353Notes

Reaction equation

HRID 591353 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]([O:27]CC)=O)[N:24]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[CH3:30][NH2:31]>CCO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:12][CH2:13][N:14]([C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]([NH:31][CH3:30])=[O:27])[N:24]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89612672HCID 89612672, compound

Product 1

HCID 72725461HCID 72725461, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
39 °C

Procedure

In a flask was placed ethyl 2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)thiazole-4-carboxylate (83.6 mg, 0.2 mmol) and EtOH (2 mL) was added. Then, 40 wt % CH3NH2(aq) (10 mL) was added and the resulting mixture was heated to 38-40° C. for 4 h. The resulting mixture was concentrated to remove EtOH and then partitioned in CH2Cl2/H2O (30 mL/30 mL). The aqueous layer was extracted with CH2Cl2 (30 mL). The combined organic layer was dried (Na2SO4) and filtered. The solvent was removed by roto-evaporator and the resulting residue re-solidified from CH2Cl2/hexane to yield 2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)-N-methylthiazole-4-carboxamide as a white solid.

Workup

  1. customIn a flask was placed
  2. concentrationThe resulting mixture was concentrated
  3. customto remove EtOH
  4. custompartitioned in CH2Cl2/H2O (30 mL/30 mL)
  5. extractionThe aqueous layer was extracted with CH2Cl2 (30 mL)
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvent was removed by roto-evaporator

Sources & evidence

ORD record
ord-f1131c6d492d43d589ca7f02aba48393
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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