Benzaldehyde → HCID 78079303, compound

HRID 2207530Notes

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](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.N1CCCCC1>C(O)C>[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:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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

Conditions

Temperature: 70 °C

Procedure

Into a 50-mL round-bottom flask, 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 ethanol (20 mL) and benzaldehyde (47 mg, 0.44 mmol, 1.98 equiv) and piperidine (479.5 mg, 5.63 mmol, 25.14 equiv) were added. The resulting solution was stirred for 12 h at 70° C. in an oil bath. 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 31 mg (24%) of 3-[2-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-(phenylmethylidene)-1,3-thiazolidine-2,4-dione as a light yellow solid. LC-MS: (ES, m/z): 535 (M+H)

Workup

customInto a 50-mL round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
washeluted with dichloromethane/methanol (100/1)

Sources & evidence

ORD record: ord-40cca9142b3244e4a15a345ab9e1d36e
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376438B2

Reaction notes

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