1,1'-Carbonyldiimidazole → HCID 59868542, compound

HRID 1923998Notes

Reaction equation

HRID 1923998 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][C@H:17]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[C:18](=[O:45])[NH:19][C@@H:20]([C:32](=[O:44])[NH:33][C:34]1[CH:35]=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1.[C:54]([O:58][C:59]([NH:61][CH2:62][CH2:63][NH:64][CH2:65][CH2:66][NH:67][C:68](=[O:74])[O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:60])([CH3:57])([CH3:56])[CH3:55]>C(Cl)Cl>[C:49]([O:48][C:47]([NH:46][C@H:17]([C:18](=[O:45])[NH:19][C@@H:20]([C:32](=[O:44])[NH:33][C:34]1[CH:35]=[N:36][C:37]2[C:42]([CH:43]=1)=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:30])([F:29])[F:31])=[CH:26][CH:27]=1)[CH2:16][CH2:15][CH2:14][NH:13][C:1]([N:64]([CH2:65][CH2:66][NH:67][C:68]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:74])[CH2:63][CH2:62][NH:61][C:59](=[O:60])[O:58][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:2])=[O:53])([CH3:50])([CH3:52])[CH3:51]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 15157893tert-butyl N-{2-[(2-{[(tert-butoxy)carbonyl]amino}ethyl)amino]ethyl}carbamateHCID 59366655HCID 59366655, compound

Product 1

HCID 59868542HCID 59868542, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of carbonyldiimidazole (204 mg, 1.25 mmol) in DCM (20 mL) was added tert-butyl N-[(1S)-4-amino-1-{[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamoyl}butyl]carbamate CXV (687 mg, 1.20 mmol) and stirred at r.t. for 1 h. To this mixture was added tert-butyl N-{2-[(2-{[(tert-butoxy)carbonyl]amino}ethyl)amino]ethyl}carbamate X (436 mg, 1.44 mmol) and the reaction was stirred overnight at r.t. The mixture was diluted DCM and washed with 1 M HCl, brine, dried over MgSO4 and purified on a silica gel column (100:1→70:1→50:1 CHCl3/MeOH) to give product tert-butyl N-[2-({[(4S)-4-{[(tert-butoxy)carbonyl]amino}-4-{[(1R)-1-[(quinolin-3-yl)carbamoyl]-2-[4-(trifluoromethyl)phenyl]ethyl]carbamoyl}butyl]carbamoyl} (2-{[(tert-butoxy)carbonyl]amino}ethyl)amino)ethyl]carbamate CXVI (500 mg, 0.55 mmol, 44% yield). ESIMS found for C44H61F3N8O9 m/z 904 (M+H).

Workup

  1. stirringthe reaction was stirred overnight at r.t
  2. washwashed with 1 M HCl, brine
  3. dry with materialdried over MgSO4
  4. custompurified on a silica gel column (100:1→70:1→50:1 CHCl3/MeOH)

Sources & evidence

ORD record
ord-3f75b72d2cf241918e8d5428b03439a1
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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