Ammonia → HCID 58430896, compound

HRID 1040548Notes

Reaction equation

HRID 1040548 reaction equation
[C:1]([C:3]1[CH:45]=[CH:44][C:6]([CH2:7][C@@:8]2([CH3:43])[N:12]3[C:13]([C:16]([NH:18][C:19]4([C:22]([NH:24][C@@H:25]5[CH2:29][CH2:28][C@H:27]([C:30](OC)=[O:31])[CH2:26]5)=[O:23])[CH2:21][CH2:20]4)=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:34]3[CH:39]=[C:38]([Cl:40])[CH:37]=[C:36]([Cl:41])[CH:35]=3)[C:9]2=[O:42])=[CH:5][CH:4]=1)#[N:2].[NH3:46]>>[C:30]([C@H:27]1[CH2:28][CH2:29][C@@H:25]([NH:24][C:22]([C:19]2([NH:18][C:16]([C:13]3[N:12]4[C@@:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:45][CH:44]=5)([CH3:43])[C:9](=[O:42])[N:10]([C:34]5[CH:39]=[C:38]([Cl:40])[CH:37]=[C:36]([Cl:41])[CH:35]=5)[C:11]4=[N:15][CH:14]=3)=[O:17])[CH2:21][CH2:20]2)=[O:23])[CH2:26]1)(=[O:31])[NH2:46]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 58431021HCID 58431021, compound

Product 1

HCID 58430896HCID 58430896, compoundYield 55%

Conditions

Temperature
80 °C

Procedure

To methyl (1S,3R)-3-({[1-({[(3R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[1,2-a]imidazol-5-yl]carbonyl}amino)cyclopropyl]-carbonyl}amino)cyclopentanecarboxylate (109.2 mg, 0.168 mmol) was added ammonia (7N in methanol, 4 mL, 28 mmol) and the reaction tube was sealed. The reaction solution was stirred at 80° C. for 65 h. The reaction solution was then cooled to room temperature and concentrated in vacuo. The resultant residue was purified via reverse phase HPLC to afford 58.6 mg of the title compound as a white solid, m/z 634.2 [M+1]+.

Workup

  1. customthe reaction tube was sealed
  2. temperatureThe reaction solution was then cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-cb07c90e2b4f4b1cba09007582b5df7f
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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