Benzamide, 3-amino-4-methoxy- → HCID 86633974, compound

HRID 1687556Notes

Reaction equation

HRID 1687556 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH2:7])=[O:6].[Cl:13][C:14]1[N:19]=[C:18](Cl)[C:17]([Cl:21])=[CH:16][N:15]=1>O1CCCC1>[Cl:13][C:14]1[N:19]=[C:18]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[O:11][CH3:12])[C:5]([NH2:7])=[O:6])[C:17]([Cl:21])=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 87135Benzamide, 3-amino-4-methoxy-HCID 2372592,4,5-Trichloropyrimidine

Product 1

HCID 86633974HCID 86633974, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-4-methoxy-benzamide (1.00 g, 0.00602 mol) in tetrahydrofuran (40 mL) was treated with 2,4,5-trichloro-pyrimidine (0.8278 mL, 0.007221 mol), and the reaction was stirred overnight at room temperature, then for 4 hours at 50° C. The mixture was partitioned between water and dichloromethane, and the aqueous phase was extracted twice with dichloromethane. The organics were dried (MgSO4) and concentrated, and the product was isolated by chromatography (Silica, MeOH/dichloromethane 0-3%), followed by crystallization from methanol to give 3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methoxy-benzamide as a white solid (1.26 g, 64%). LC/MS (ESI+): 313.04 (M+H).

Workup

  1. waitfor 4 hours at 50° C
  2. customThe mixture was partitioned between water and dichloromethane
  3. extractionthe aqueous phase was extracted twice with dichloromethane
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe product was isolated by chromatography (Silica, MeOH/dichloromethane 0-3%)
  7. customfollowed by crystallization from methanol

Sources & evidence

ORD record
ord-8d2de9a9c01448178cb1c707e30b64d9
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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