Diisopropylethylamine → HCID 90308957, compound

HRID 2283666Notes

Reaction equation

HRID 2283666 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:14])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:26]1[N:27]=[N:28][C:29]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:30]([NH:32][C:33]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:34]=2[CH:35]=[CH:36][N:37]3[CH3:42])[N:31]=1>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH:14][C:26]1[N:27]=[N:28][C:29]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:30]([NH:32][C:33]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:34]=2[CH:35]=[CH:36][N:37]3[CH3:42])[N:31]=1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 90308765HCID 90308765, compound

Product 1

HCID 90308957HCID 90308957, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl((1S,2R)-2-aminocyclohexyl)carbamate (302 mg) and diisopropylethylamine (0.40 ml) were added successively to a solution of ethyl 3-chloro-5-(1-methyl-1H-indol-4-ylamino)-1,2,4-triazine-6-carboxylate (390 mg) obtained in the above-described Step 1 in THF (10 ml), and the reaction solution was allowed to react at 70° C. for 2 hours. The reaction solution was diluted with ethyl acetate, washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum, and the resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain ethyl 3-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-(1-methyl-1H-indol-4-ylamino)-1,2,4-triazine-6-carboxylate as a yellow solid.

Workup

  1. customto react at 70° C. for 2 hours
  2. washwashed successively with an aqueous sodium bicarbonate solution
  3. dry with materiala saturated saline solution, and then dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under vacuum
  5. customthe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-29aac5a9e3a54ef4b44a03a28d7c463d
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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