Water → 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 711111Notes

Reaction equation

HRID 711111 reaction equation
C(N=C=[N:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:11])C)C.ON1[C:17]2[CH:18]=CC=[CH:21][C:16]=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].O.CN(C)[CH:44]=[O:45]>>[CH:23]([N:26]1[C:30]2[C:31](=[O:40])[NH:32][C:33]3([CH2:39][CH2:38][N:37]([C:44]([C:16]4[CH:17]=[CH:18][C:6]5[C:7](=[CH:8][N:9]([CH3:11])[N:5]=5)[CH:21]=4)=[O:45])[CH2:36][CH2:35]3)[CH2:34][C:29]=2[CH:28]=[N:27]1)([CH3:25])[CH3:24]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 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 hydrochloride

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

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-4,6-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-cd19d3f9a3764a7e8d9068be02165f71
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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