Water → HCID 67125913, compound

HRID 929960Notes

Reaction equation

HRID 929960 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21](O)=[O:22])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:46][C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:54]([NH:56][C:57]2[CH:61]=[C:60]([C:62]([CH3:65])([CH3:64])[CH3:63])[O:59][N:58]=2)=[O:55])=[CH:49][CH:48]=1.O>CN(C=O)C>[C:62]([C:60]1[O:59][N:58]=[C:57]([NH:56][C:54](=[O:55])[NH:53][C:50]2[CH:49]=[CH:48][C:47]([NH:46][C:21]([C:17]3[CH:16]=[C:15]([O:14][CH:11]4[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]4)[CH:20]=[CH:19][N:18]=3)=[O:22])=[CH:52][CH:51]=2)[CH:61]=1)([CH3:65])([CH3:63])[CH3:64]

Participants

6

Reactant 4

HCID 962WaterHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59380899HCID 59380899, compoundHCID 67125878HCID 67125878, compound

Product 1

HCID 67125913HCID 67125913, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1-(tert-Butoxycarbonyl)piperidin-4-yloxy)picolinic acid from Step 2 (188 mg, 0.58 mmol) was stirred in 3 mL of DMF. TBTU (244 mg, 0.76 mmol) was added, followed by TEA (82 μL, 0.058 mmol). After 10 min, 1-(4-aminophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (Ref: Milanov, Zdravko V. et al. WO2005/48948 A2, 2005 Jun. 2) (160 mg, 0.58 mmol) was added, followed by TEA (82 μL, 0.058 mmol). The resulting mixture was stirred at rt for 3 h. LC-MS indicated that the reaction was complete. Water (20 mL) was then added, the precipitates were collected by filtration and washed with cold water, dried in vacuum oven to give tert-butyl 4-(2-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenylcarbamoyl)pyridin-4-yloxy)piperidine-1-carboxylate (280 mg, 83%) as an off-white solid. LC-MS (ESI) m/z 579 (M+H)+.

Workup

  1. filtrationthe precipitates were collected by filtration
  2. washwashed with cold water
  3. customdried in vacuum oven

Sources & evidence

ORD record
ord-0654d6a2915e478dbc7a5b4b3a2ceccc
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

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