HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

1,2-Diaminocyclohexane, trans- → N-[4-amino-3-(4-amino-3-methoxyphenyl)thieno[3,2-c]pyridin-7-yl]-2-pyrrolidin-1-ylacetamide triacetate salt

HRID 17231
Notes
Print preview

Reaction equation

HRID 17231 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13]([NH2:18])=[N:14][CH:15]=[C:16](I)[C:11]=3[S:10][CH:9]=2)=[CH:4][C:3]=1[O:19][CH3:20].[N:21]1([CH2:26][C:27]([NH2:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22]1.P([O-])([O-])([O-])=[O:31].[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>[Cu]I.O1CCOCC1>[C:3]([OH:19])(=[O:28])[CH3:4].[C:27]([OH:28])(=[O:31])[CH3:26].[C:3]([OH:19])(=[O:28])[CH3:4].[NH2:18][C:13]1[C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([O:19][CH3:20])[CH:4]=3)=[CH:9][S:10][C:11]=2[C:16]([NH:29][C:27](=[O:28])[CH2:26][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][N:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 134758251-PyrrolidineacetamideHCID 184507103-(4-Amino-3-methoxyphenyl)-7-iodothieno[3,2-c]pyridin-4-amine

Product 1

HCID 18451403N-[4-amino-3-(4-amino-3-methoxyphenyl)thieno[3,2-c]pyridin-7-yl]-2-pyrrolidin-1-ylacetamide triacetate salt

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A schlenck tube was charged with 3-(4-amino-3-methoxyphenyl)-7-iodothieno[3,2-c]pyridin-4-amine (199 mg, 0.5 mmol), 2-pyrrolidin-1-ylacetamide (0.6 mmol), copper(I) iodide (4.8 mg, 0.025 mmol), potassium phosphate (225 mg, 1.06 mmol). Evacuated under vacuum and back filled with nitrogen. trans-Cyclohexane-1,2-diamine (6.5 uL, 0.05 mmol) and dioxane (1 mL) was added. The reaction tube was sealed and heated at about 110° C. overnight. The solvent was removed and the crude product was purified by reverse phase preparative HPLC to give the title compound as the tri-acetate salt. LCMS (Conditions a): MH+=398.2, Rt=1.55 min. (154 mg, 45%)

Workup

  1. customEvacuated under vacuum
  2. additionback filled with nitrogen
  3. customThe reaction tube was sealed
  4. customThe solvent was removed
  5. customthe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-a1656f847d5b4166abc0cb76fd0c498c
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737160B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes