1-Benzyloxycarbonyl-2-(1-aminoethyl)-4-tert-butyloxycarbonylpiperazine → HCID 70123251, compound

HRID 429287Notes

Reaction equation

HRID 429287 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[C:5]([Br:17])=[CH:4][N:3]=1.[CH2:18]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH:29]1[CH:41]([NH2:43])[CH3:42])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH2:18]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:30][CH:29]1[CH:41]([NH:43][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[C:5]([Br:17])=[CH:4][N:3]=1)[CH3:42])=[O:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 183428831-Benzyloxycarbonyl-2-(1-aminoethyl)-4-tert-butyloxycarbonylpiperazineHCID 22731922HCID 22731922, compound

Product 1

HCID 70123251HCID 70123251, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-4-(benzimidazol-1-yl)-5-bromopyrimidine (100 mg) and 1-benzyloxycarbonyl-2-(1-aminoethyl)-4-tert-butyloxycarbonylpiperazine, diastereomer 1 (EXAMPLE 14 Step D; 115 mg), in 10 mL of toluene was heated to 100° C. and stirred overnight (14 h) at this temperature. The mixture was then cooled and diluted with 20 mL of EtOAc and 30 mL of water. The phases were separated and the aqueous phase was extracted with 2×20 mL of EtOAc. The combined organics were dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 20:1 hexanes-acetone to provide 133 mg of the title compound. Mass spectrum (ESI) 638.4 (M+1).

Workup

  1. temperatureThe mixture was then cooled
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with 2×20 mL of EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 20:1 hexanes-acetone

Sources & evidence

ORD record
ord-218e18bef09e40be99eff1991c35638c
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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