Sodium Bicarbonate → 2-{4-[2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyanopyridin-4-yl]-piperidin-1-yl}-2-oxoethyl acetate

HRID 1873574Notes

Reaction equation

HRID 1873574 reaction equation
[C:1]([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([C:20]#[N:21])=[C:18]([SH:22])[N:17]=[C:16]([NH2:23])[C:15]=2[C:24]#[N:25])[CH2:10][CH2:9]1)=[O:7])(=[O:3])[CH3:2].Cl[CH2:27][C:28]1[N:29]=[C:30]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[S:31][CH:32]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:1]([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:19]([C:20]#[N:21])=[C:18]([S:22][CH2:27][C:28]3[N:29]=[C:30]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=4)[S:31][CH:32]=3)[N:17]=[C:16]([NH2:23])[C:15]=2[C:24]#[N:25])[CH2:10][CH2:9]1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 178476478HCID 178476478, compound

Product 1

HCID 687021312-{4-[2-Amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyanopyridin-4-yl]-piperidin-1-yl}-2-oxoethyl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

34 mg (0.06 mmol) of the compound from Example 24A are dissolved in 1.2 ml of dry DMF, and 17 mg (0.07 mmol) of 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole and 19 mg (0.23 mmol) of sodium bicarbonate are added. The reaction mixture is stirred at RT for 8 h. The mixture is then filtered, and about 0.5 ml of water is added to the filtrate. The precipitate formed is filtered off with suction and dried under reduced pressure at +50° C.

Workup

  1. filtrationThe mixture is then filtered
  2. additionabout 0.5 ml of water is added to the filtrate
  3. customThe precipitate formed
  4. filtrationis filtered off with suction
  5. customdried under reduced pressure at +50° C.

Sources & evidence

ORD record
ord-808f51f1d05b4497b1c1c2c855bd4334
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

Loading…