1,1-Dichloroethane → HCID 178437677, compound

HRID 869276Notes

Reaction equation

HRID 869276 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]([NH2:11])=[O:10])[C:6]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[N:5][C:4]=1[NH:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([OH:32])[CH2:28][CH2:27]1)[CH3:2].ClC(Cl)C.[C:37](OC(=O)C)(=[O:39])[CH3:38].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:37]([N:22]1[CH2:21][CH2:20][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:6]3[C:7]([C:9]([NH2:11])=[O:10])=[N:8][C:3]([CH2:1][CH3:2])=[C:4]([NH:25][C@H:26]4[CH2:27][CH2:28][C@H:29]([OH:32])[CH2:30][CH2:31]4)[N:5]=3)=[CH:14][CH:15]=2)[CH2:24][CH2:23]1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178437675HCID 178437675, compound

Product 1

HCID 178437677HCID 178437677, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 6-ethyl-5-[(trans-4-hydroxycyclohexyl)amino]-3-[(4-piperidin-4-ylphenyl)amino]pyrazine-2-carboxamide (Example 358) (43 mg) and dichloroethane (1 mL), pyridine (0.01 mL) and acetic anhydride (0.01 mL) were added under ice cooling and stirred at room temperature for 20 minutes. After addition of saturated aqueous sodium hydrogen carbonate, the reaction liquid was partitioned using chloroform and saturated aqueous sodium hydrogen carbonate. After drying over anhydrous sodium sulfate, the organic layer was concentrated, and the resulting residue was solidified with ethyl acetate-hexane to give 3-{[4-(1-acetylpiperidin-4-yl)phenyl]amino}-6-ethyl-5-[(trans-4-hydroxycyclohexyl)amino]pyrazine-2-carboxamide (26 mg) as a white solid.

Workup

  1. additionwere added under ice cooling
  2. customthe reaction liquid
  3. customwas partitioned
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-40beef5deb054cb8aaaa1b52c1e52e19
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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