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

HRID 1041248Notes

Reaction equation

HRID 1041248 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-180297a366f04fa8867061fcae7221ad
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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