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Water → 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamide

HRID 1773627
Notes
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Reaction equation

HRID 1773627 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:18]4[N:19]=[C:20](Cl)[N:21]=[CH:22][C:17]=4[S:16][CH:15]=3)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C@@H:24]1([NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[NH2:30].O.ClCCl>O1CCOCC1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:18]4[N:19]=[C:20]([NH:30][C@@H:25]5[CH2:26][CH2:27][CH2:28][CH2:29][C@@H:24]5[NH2:31])[N:21]=[CH:22][C:17]=4[S:16][CH:15]=3)=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 3429171,2-Diaminocyclohexane, cis-HCID 866613802-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamide

Product 1

HCID 566465512-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamideYield 55.4%

Reagents, catalysts & solvents

1
HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.0794 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamide in 2.33 mL of dioxane was added 0.168 mL (1.4 mmole) of cis-cyclohexane-1,2-diamine. The mixture was heated at 100 degrees for 2 hours. Water and dichloromethane were added, separated. The aqueous layer was washed with dichloromethane twice. The organic layer was washed with aqueous sodium carbonate, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10) gave 0.054 g of 2-(cis-2-amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid quinolin-6-ylamide as a light yellow solid. MH+/Z=419.

Workup

  1. temperatureThe mixture was heated at 100 degrees for 2 hours
  2. customseparated
  3. washThe aqueous layer was washed with dichloromethane twice
  4. washThe organic layer was washed with aqueous sodium carbonate, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography
  9. washeluting with dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10)

Sources & evidence

ORD record
ord-c376ce930ad44d8eabf268dc3571f06f
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09255110B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes