1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1'-isopropyl-1-(2-methyl-2H-indazole-5-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(1'H)-one

HRID 881007Notes

Reaction equation

HRID 881007 reaction equation
C(N=C=NCCCN(C)C)C.[OH:12]N1C2C=CC=CC=2N=N1.Cl.[CH:23]([N:26]1[C:30]2[C:31](=[O:40])[NH:32][C:33]3([CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[CH2:34][C:29]=2[CH:28]=[N:27]1)([CH3:25])[CH3:24].[CH:41]([N:44]1[C:48]2C(=O)N[C:51]3([CH2:57]CN[CH2:54][CH2:53]3)[CH2:52][C:47]=2[CH:46]=[N:45]1)(C)C>CN(C)C=O.O>[CH:23]([N:26]1[C:30]2[C:31](=[O:40])[NH:32][C:33]3([CH2:39][CH2:38][N:37]([C:57]([C:51]4[CH:53]=[CH:54][C:46]5[C:47](=[CH:48][N:44]([CH3:41])[N:45]=5)[CH:52]=4)=[O:12])[CH2:36][CH2:35]3)[CH2:34][C:29]=2[CH:28]=[N:27]1)([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 674915351'-Isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(1'H)-one hydrochlorideHCID 674915361'-isopropyl-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(1'H)-one

Product 1

HCID 569676371'-isopropyl-1-(2-methyl-2H-indazole-5-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(1'H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-2H-indazole-5-carboxyllic acid (28 mg, 0.16 mmol) in dry dimethylformamide was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (37 mg, 0.19 mmol) and 1-hydroxybenzotriazole (26 mg, 0.19 mmol) N,N-diisopropylethylamine (84 μL, 0.48 mmol). The reaction mixture was stirred at room temperature for 10 minutes and then 1′-isopropyl-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(1′H)-one hydrochloride was added (Intermediate 2, 30 mg, 0.12 mmol) and the reaction was stirred for 16 hours. The mixture was poured into chilled water and the resulting precipitate was collected by vacuum filtration. The obtained solid was triturated from diethyl ether to afford 1′-isopropyl-1-(2-methyl-2H-indazole-5-carbonyl)-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(1′H)-one (25 mg). +ESI (M+H) 407.3; 1H NMR (400 MHz, DMSO-d6, δ): 8.41 (s, 1H), 7.85 (s, 1H), 7.75 (s, 1H), 7.63 (d, 1H), 7.40 (s, 1H), 7.20 (s, 1H), 5.40 (m, 1H), 4.18 (s, 3H), 3.60 (br. s., 4H), 2.85 (s, 2H), 1.70 (br. s., 4H), 1.35 (d, 6H).

Workup

  1. stirringthe reaction was stirred for 16 hours
  2. additionThe mixture was poured
  3. filtrationthe resulting precipitate was collected by vacuum filtration
  4. customThe obtained solid was triturated from diethyl ether

Sources & evidence

ORD record
ord-838873937ab74e58ba6c0d38bbf89298
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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