Water → HCID 178427120, compound

HRID 1486481Notes

Reaction equation

HRID 1486481 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([NH2:19])[CH2:15][CH2:14]1.[CH3:20][C:21]1[O:25][N:24]=[C:23]([C:26](O)=[O:27])[CH:22]=1.C(P(O)(=O)O)CC.O>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([NH:19][C:26]([C:23]2[CH:22]=[C:21]([CH3:20])[O:25][N:24]=2)=[O:27])[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 204484Propylphosphonic acidHCID 178511708HCID 178511708, compound

Product 1

HCID 178427120HCID 178427120, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

trans-4-[(8-Bromoquinolin-4-yl)oxy]cyclohexylamine (321 mg, 1.0 mmol), and 5-methylisoxazole-3-carboxylic acid (153 mg, 1.2 mmol) were put in pyridine (4.0 mL) and propanephosphonic acid cycloanhydride (637 mg, 2.0 mmol) was added. The reaction mixture was stirred overnight at room temperature. Water was added until a precipitate formed. After a further 10 minutes the precipitate was filtered off with suction and washed with water. After drying, the desired compound was obtained at 92% yield (400 mg).

Workup

  1. customformed
  2. filtrationAfter a further 10 minutes the precipitate was filtered off with suction
  3. washwashed with water
  4. customAfter drying

Sources & evidence

ORD record
ord-c492b23bf87049488e311252f6d2f8f5
Source dataset
uspto-grants-2016_08
Patent number
US09428460B2

Reaction notes

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