5-Bromosalicylic acid → HCID 68547977, compound

HRID 2241916Notes

Reaction equation

HRID 2241916 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12]([O:16][C:17](=[O:33])[NH:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:26]=2[F:32])[CH2:21][CH2:20]1)([CH3:15])([CH3:14])[CH3:13].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O.CN(C)C=O>[C:12]([O:16][C:17](=[O:33])[NH:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:7](=[O:9])[C:6]3[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[OH:11])=[CH:27][C:26]=2[F:32])[CH2:21][CH2:20]1)([CH3:15])([CH3:13])[CH3:14]

Participants

9

Reactant 6

HCID 69725-Bromosalicylic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59205047HCID 59205047, compound

Product 1

HCID 68547977HCID 68547977, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromosalicylic acid (326 mg, 1.5 mmol), [1-(4-amino-2-fluorophenyl)piperidin-4-yl]carbamic acid tert-butyl ester (compound of Reference Example 90; 309 mg, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (287 mg, 1.5 mmol), 1-hydroxybenzotriazole (202 mg, 1.5 mmol), triethylamine (210% 1, 1.5 mmol) and N,N-dimethylformamide (5 ml) was stirred at room temperature for 3 hours. Saturated aqueous sodium hydrogen carbonate and water was added to the reaction mixture and the mixture was carried out ultrasound irradiation. The precipitated solid was collected by filtration and washed with water. The solid was suspended in methanol and carried out ultrasound irradiation. The solid was collected by filtration and dried under reduced pressure to give the title compound (224 mg, 47%) as a white solid.

Workup

  1. customirradiation
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customirradiation
  5. filtrationThe solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-630709845b834c308f70909ed056f95e
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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