Triethylamine → HCID 71657232, compound

HRID 591347Notes

Reaction equation

HRID 591347 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][NH:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[N+](C1C=CC([N:26]([C:30]2[S:31][CH:32]=[C:33]([CH3:35])[N:34]=2)[C:27](=O)[O-:28])=CC=1)([O-])=O.CCN(CC)CC.CCOC(C)=O.O>C(Cl)Cl>[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:27]([NH:26][C:30]3[S:31][CH:32]=[C:33]([CH3:35])[N:34]=3)=[O:28])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 220383846-Fluoro-1-(piperidin-4-yl)indolineHCID 22728543Water ethylacetateHCID 118656493HCID 118656493, compound

Product 1

HCID 71657232HCID 71657232, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-fluoro-1-(piperidin-4-yl)indoline, prepared as in STEP 2 above (128 mg, 0.5 mmol) and 4-nitrophenyl(4-methylthiazol-2-yl)carbamate, prepared as in STEP 3 above (186 mg, 0.4 mmol, ca. 60% purity) in CH2Cl2 (3 mL) was added Et3N (0.28 mL, 2 mmol) at room temperature. The resulting mixture was stirred at room temperature for 3 h and was poured into EtOAc/H2O (20 mL/20 mL). The organic layer was dried (Na2SO4) and filtered. The solvent was removed by roto-evaporator and the resulting residue purified by silica gel chromatography using 40% EtOAc/hexane as the eluent to yield 4-(6-fluoroindolin-1-yl)-N-(4-methylthiazol-2-yl)piperidine-1-carboxamide as a white solid.

Workup

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. filtrationfiltered
  3. customThe solvent was removed by roto-evaporator
  4. customthe resulting residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-3ee79b6085474b5f92c3ef62707c254c
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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