Methylamine → HCID 131726322, compound

HRID 1270002Notes

Reaction equation

HRID 1270002 reaction equation
CN.O=C1C2C(=CC=CC=2)C(=O)[N:5]1[CH2:14][C:15]([NH:17][C@H:18]1[CH2:23][CH2:22][CH2:21][C@@H:20]([O:24][C:25]2[C:26]([CH3:34])=[C:27]3[C:31](=[CH:32][CH:33]=2)[NH:30][N:29]=[CH:28]3)[CH2:19]1)=[O:16].[ClH:35].CC1C(O[C@@H]2CCC[C@H](NCC(N)=O)C2)=CC=C2C=1C=NN2>>[ClH:35].[CH3:34][C:26]1[C:25]([O:24][C@@H:20]2[CH2:21][CH2:22][CH2:23][C@H:18]([NH:17][C:15](=[O:16])[CH2:14][NH2:5])[CH2:19]2)=[CH:33][CH:32]=[C:31]2[C:27]=1[CH:28]=[N:29][NH:30]2

Participants

4

Reactant 3

HCID 6329MethylamineHCID 69428534HCID 69428534, compoundHCID 131726324HCID 131726324, compound

Product 1

HCID 131726322HCID 131726322, compound

Procedure

A 40% methylamine methanolic solution (5 mL) was added to the 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-{cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}acetamide (70 mg, 0.16 mmol) obtained in Example 825, and the resulting mixture was stirred overnight. The reaction solution was distilled under reduced pressure to remove the solvent and then the residue was purified by a silica gel chromatography. To a solution of the purified residue in 2-propanol was added a hydrochloric acid-diethyl ether solution, and stirred for 30 minutes. After the solvent was distilled off under reduced pressure, the residue was crystallized from 2-propanol-diisopropyl ether-diethyl ether to obtain N˜1˜(identification is required)-{cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}glycinamide monohydrochloride (39 mg, 79%).

Workup

  1. distillationThe reaction solution was distilled under reduced pressure
  2. customto remove the solvent
  3. customthe residue was purified by a silica gel chromatography
  4. additionTo a solution of the purified residue in 2-propanol was added a hydrochloric acid-diethyl ether solution
  5. stirringstirred for 30 minutes
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. customthe residue was crystallized from 2-propanol-diisopropyl ether-diethyl ether
  8. customto obtain N˜1˜(identification

Sources & evidence

ORD record
ord-cee442437e0a4a7a8f340385bb92cc7f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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