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Sulfamide → HCID 178527251, compound

HRID 715629
Notes
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Reaction equation

HRID 715629 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1)[N:13]=[CH:12][N:11]=2.[S:31](N)([NH2:34])(=[O:33])=[O:32]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][NH:34][SH:31](=[O:33])=[O:32])[CH2:19][CH2:18]1)[N:13]=[CH:12][N:11]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 82267SulfamideHCID 715144901-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-amine

Product 1

HCID 178527251HCID 178527251, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-amine (36.6 mg, 0.083 mmol, 1 eq.) in 2 mL of dioxane was added sulfamide (40 mg, 0.42 mmol, 5 eq.). The reaction was heated to 80° C. for 16 h. The reaction was concentrated in vacuo. The crude material was purified by silica gel column chromatography using 0-100% ethyl acetate/hexane to yield 34 mg (79%) of desired compound. 1H NMR (300 MHz, METHANOL-d4) δ ppm 1.51-1.72 (m, 2 H) 2.15 (br. s., 2 H) 3.38-3.52 (m, 2 H) 3.54-3.65 (m, 1 H) 5.18-5.41 (m, 2 H) 7.24-7.50 (m, 7 H) 7.54-7.67 (m, 1 H) 8.23 (s, 1 H), [M+h]+ 518.5.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d400afc91ad94d9699ba133d58add003
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187480B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes