Methylamine → HCID 72725462, compound

HRID 591354Notes

Reaction equation

HRID 591354 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][C:22]([C:25]([O:27]C)=O)=[CH:23][N:24]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[CH3:29][NH2:30]>CO>[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][C:22]([C:25]([NH:30][CH3:29])=[O:27])=[CH:23][N:24]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89612782HCID 89612782, compound

Product 1

HCID 72725462HCID 72725462, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
39 °C

Procedure

In a flask was placed methyl 2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)thiazole-5-carboxylate (80.8 mg, 0.2 mmol) and MeOH (4 mL) was added. Then, 40 wt % CH3NH2(aq) (6 mL) was added and the resulting mixture was heated to 38-40° C. for 4 h. The resulting mixture was concentrated to remove MeOH 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-5-carboxamide as a white solid.

Workup

  1. customIn a flask was placed
  2. concentrationThe resulting mixture was concentrated
  3. customto remove MeOH
  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-e53979b1d99948b7a6fe7f216c376e7e
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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