Triethylamine → HCID 118036954, compound

HRID 2206883Notes

Reaction equation

HRID 2206883 reaction equation
[CH3:1][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH2:4][C:3]21[CH2:15][CH2:14][CH2:13][CH2:12]2.C(N(CC)CC)C.[Cl:23][C:24]1[N:28]([CH3:29])[N:27]=[C:26]([CH:30]([F:32])[F:31])[C:25]=1[C:33](Cl)=[O:34]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:23][C:24]1[N:28]([CH3:29])[N:27]=[C:26]([CH:30]([F:31])[F:32])[C:25]=1[C:33]([NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][C:3]1([CH2:12][CH2:13][CH2:14][CH2:15]1)[CH:2]2[CH3:1])=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86663089HCID 86663089, compoundHCID 118037152HCID 118037152, compound

Product 1

HCID 118036954HCID 118036954, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a 25 ml round bottom flask, a solution of 1′-methyl-1′,3′-dihydrospiro[cyclopentane-1,2′-inden]-4′-amine in 5 ml of DCM is cooled to 0° C. and triethylamine (0.104 ml, 0.745 mmol, 1.5 eq) is added followed by DMAP (6 mg, 0.05 mmol, 0.1 eq). A solution of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride (125 mg, 0.546 mmol, 1.1 eq) in 1 ml of DCM is added dropwise. Stirring is allowed for 4 h at r.t. The reaction is quenched with 1N aq. HCl, and diluted with EtOAc. The aqueous layer was separated and extracted with EtOAc. The organics were combined, washed with NaOH 1N, dried over MgSO4 and concentrated. The crude material was purified by chromatography on silica gel to give pure material (64%)

Workup

  1. customThe reaction is quenched with 1N aq. HCl
  2. additiondiluted with EtOAc
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. washwashed with NaOH 1N
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-933174ecdd3d4fb4a16d9fb86ef2a6d5
Source dataset
uspto-grants-2016_06
Patent number
US09375005B2

Reaction notes

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