1,1-Dichloroethane → HCID 70157383, compound

HRID 2303311Notes

Reaction equation

HRID 2303311 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:23]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1/[CH:33]=[CH:34]\[C:35]([OH:37])=O)(=[O:25])[CH3:24].ClC(Cl)C.[NH2:42][C@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][C@H:44]1[NH:49][C:50]1[N:55]=[C:54]([NH:56][C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([CH3:63])[CH:58]=2)[C:53]([C:64]([NH2:66])=[O:65])=[CH:52][N:51]=1>O.CN(C=O)C>[C:23]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1/[CH:33]=[CH:34]\[C:35](=[O:37])[NH:42][C@@H:43]1[CH2:48][CH2:47][CH2:46][CH2:45][C@@H:44]1[NH:49][C:50]1[N:55]=[C:54]([NH:56][C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([CH3:63])[CH:58]=2)[C:53]([C:64](=[O:65])[NH2:66])=[CH:52][N:51]=1)(=[O:25])[CH3:24]

Participants

8

Reactant 5

HCID 63651,1-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114938412-{[(1R,2S)-2-Aminocyclohexyl]amino}-4-(3-methylanilino)pyrimidine-5-carboxamideHCID 25021207HCID 25021207, compound

Product 1

HCID 70157383HCID 70157383, compoundYield 19.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 135 mg portion of HOBt and 192 mg of WSC·HCl were added to a mixture of 195 mg of (Z)-3-[2-(acetoxy)phenyl]acrylic acid and 10 ml of dichloroethane, followed by stirring for 20 minutes under ice-cooling. Then, 2 ml of DMF solution containing 340 mg of 2-(cis-2-aminocyclohexylamino)-4-(3-methylanilino)pyrimidine-5-carboxamide was added, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent; chloroform:methanel) and then the thus obtained colorless solid was recrystallized from ethyl acetate, thereby obtaining 98 mg of 2-{(Z)-2-[(cis-2-{[5-carbamoyl-4-(3-methylanilino)pyrimidin-2-yl]amino}cyclohexyl)carbamoyl]vinyl}phenyl acetate (colorless crystals).

Workup

  1. temperaturecooling
  2. additionwas added
  3. stirringby stirring at room temperature for 2 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluting solvent; chloroform:methanel)
  8. customthe thus obtained colorless solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fe088ac208c24006b650dfc5a112eb6b
Source dataset
uspto-grants-2002_08
Patent number
US06432963B1

Reaction notes

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