Dichloromethane → HCID 78079304, compound

HRID 2207531Notes

Reaction equation

HRID 2207531 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:24][CH2:25][N:26]3[C:30](=[O:31])[CH2:29][S:28][C:27]3=[O:32])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)[C:3]=12.[CH:33]1([CH:36]=O)[CH2:35][CH2:34]1.N1CCCCC1.ClCCl>CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:24][CH2:25][N:26]3[C:30](=[O:31])[C:29](=[CH:36][CH:33]4[CH2:35][CH2:34]4)[S:28][C:27]3=[O:32])[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:15][CH:16]=3)[C:3]=12

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8082PiperidineHCID 123114CyclopropanecarboxaldehydeHCID 89189131HCID 89189131, compound

Product 1

HCID 78079304HCID 78079304, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 50-mL scaled tube, was placed a solution of 3-[2-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-1,3-thiazolidine-2,4-dione (100 mg, 0.22 mmol, 1.00 equiv) in methanol (20 mL), cyclopropanecarbaldehyde (47 mg, 0.67 mmol, 2.99 equiv), piperidine (9.5 mg, 0.11 mmol, 0.50 equiv), dichloromethane (5 mL). The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (100/1) to give 28 mg (24%) of 3-[2-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-(cyclopropylmethylidene)-1,3-thiazolidine-2,4-dione as a white solid. LC-MS (ES, m/z): 499 (M+H)+

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. washeluted with dichloromethane/methanol (100/1)

Sources & evidence

ORD record
ord-3524b3e804174f3dbbb5ef93fbf38d3a
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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