Hydrochloric Acid → HCID 54760983, compound

HRID 929998Notes

Reaction equation

HRID 929998 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11](=[O:40])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:39])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:28]4C(=O)C5C(=CC=CC=5)C4=O)[N:22]=3)=[CH:15][CH:14]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.NN.[ClH:44]>C(O)C.CCOCC>[ClH:44].[NH2:28][CH2:27][C:23]1[N:22]=[C:21]([C:20]([NH:19][C:16]2[CH:15]=[CH:14][C:13]([NH:12][C:11]([NH:10][C:7]3[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[O:9][N:8]=3)=[O:40])=[CH:18][CH:17]=2)=[O:39])[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 67125914HCID 67125914, compound

Product 1

HCID 54760983HCID 54760983, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of N-(4-(3-(5-(tert-butyl)isoxazol-3-yl)ureido)phenyl)-6-((1,3-dioxoisoindolin-2-yl)methyl)picolinamide (60 mg, 0.11 mmol) from Step 1 of this example in ethanol was heated at 70° C. until a clear solution was observed. Hydrazine hydrate (0.1 mL) was then added, the resulting mixture was heated at 70° C. for 1 h. The reaction mixture was cooled to 0° C. and filtered through celite. The filtrate was concentrated under reduced pressure, and the crude residue was purified by preparative TLC, eluting with MeOH in DCM (10:1, v:v). The compound obtained was treated with 2N HCl in Et2O to form the corresponding hydrochloric acid salt. The salt was washed with cold water and dried in a vacuum oven to afford 6-(aminomethyl)-N-(4-(3-(5-(tert-butyl)isoxazol-3-yl)ureido)phenyl)picolinamide hydrochloride (8 mg, 16%). LC-MS (ESI) m/z 409 (M+H)+.

Workup

  1. temperaturethe resulting mixture was heated at 70° C. for 1 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe crude residue was purified by preparative TLC
  6. washeluting with MeOH in DCM (10:1, v:v)
  7. customThe compound obtained

Sources & evidence

ORD record
ord-9871146c5ae1442b9207bf67028b7d35
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

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