Hydrochloric Acid → HCID 131727491, compound

HRID 1986105Notes

Reaction equation

HRID 1986105 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.Cl.N1[C:20]2=[N:21][CH:22]=[CH:23][C:24]([O:25][C:26]3[CH:31]=[CH:30][C:29]([NH:32]C4C(C(NC5C=CC(F)=CC=5F)=O)=CN=CC=4)=[CH:28][C:27]=3[F:50])=[C:19]2C=C1.Cl.O1CCOCC1.C[N:59]1[C:63](=[O:64])CCC1>O>[ClH:1].[C:63]([C:20]1[CH:19]=[C:24]([O:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:2]3[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=3)=[CH:28][C:27]=2[F:50])[CH:23]=[CH:22][N:21]=1)(=[O:64])[NH2:59]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 312751,4-DioxaneHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 162230054-(4-(1h-Pyrrolo[2,3-b]pyridin-4-yloxy)-3-fluorophenylamino)-n-(2,4-difluorophenyl)nicotinamide, hydrochloride salt2×

Product 1

HCID 131727491HCID 131727491, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (Alpha Aesar, 2.08 g, 8.93 mmol) and 4-(4-amino-2-fluorophenoxy)picolinamide (2.0 g, 8.09 mmol, Compound C of Example 3) in NMP (10 mL) was added a solution of 4 N HCl in 1,4-dioxane (4 mL, 16 mmol). After stirring overnight, the reaction mixture was diluted with water (200 mL) and the resulting solid was filtered and dried in vacuo to give the desired product (3.6 g, 93%) as a white solid. MS(ESI+) m/z 444 (M+H)+.

Workup

  1. filtrationthe resulting solid was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-9c1e8c33c621412fb9abf896854f26d5
Source dataset
uspto-grants-2009_06
Patent number
US07547782B2

Reaction notes

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