Hydrochloric Acid → HCID 21934601, compound

HRID 1241373Notes

Reaction equation

HRID 1241373 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:9]2)[CH:3]=1.[H-].[Na+].Cl[C:24]1[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=1.Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.O>[C:29]([C:26]1[S:25][C:24]([NH:1][C:2]2[N:7]=[CH:6][N:5]=[C:4]([N:8]3[CH2:13][CH2:12][CH2:11][CH:10]([NH:14][C:15](=[O:20])[C:16]([F:18])([F:17])[F:19])[CH2:9]3)[CH:3]=2)=[N:28][CH:27]=1)#[N:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934597N-[1-(6-aminopyrimidin-4-yl)piperidin-3-yl]-2,2,2-trifluoroacetamide

Product 1

HCID 21934601HCID 21934601, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[1-(6-aminopyrimidin-4-yl)piperidin-3-yl]-2,2,2-trifluoroacetamide 9-4 (0.26 g, 0.9 mmol), sodium hydride (0.144 g, 3.6 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.13 g, 0.9 mmol) were treated as in Scheme 4 above. When the reaction was complete it was quenched with 5 equivalents of concentrated HCl (370 μL). The solution was then diluted with ethyl acetate, water and some dilute NaHCO3. The aqueous layer was removed and the organic layer dried, filtered and evaporated to dryness under reduced pressure. Trituration with ethyl ether produced 9-5 as a solid, which was used without further purification in the next step.

Workup

  1. customThe aqueous layer was removed
  2. customthe organic layer dried
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9259d7ed2cdd4c33ba303ae203299e75
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…