Ammonia → HCID 66818714, compound

HRID 1024788Notes

Reaction equation

HRID 1024788 reaction equation
C(OC(N[CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]([C:18]2[CH:19]=[C:20]([CH:31]=[C:32]([O:34][C:35]3[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=3)[CH:33]=2)[O:21][C:22]2[CH:30]=[CH:29][C:25](C(O)=O)=[CH:24][CH:23]=2)=[O:17])[CH2:11][CH2:10]1)=O)(C)(C)C.C[N:44]1[CH2:49]COCC1.[C:50]([O:54][C:55](Cl)=[O:56])([CH3:53])([CH3:52])[CH3:51].[NH3:58].C1C[O:62]CC1>C(OCC)(=O)C>[C:50]([O:54][C:55](=[O:56])[NH:58][CH:9]1[CH2:10][CH2:11][CH:12]([NH:15][C:16](=[O:17])[C:18]2[CH:33]=[C:32]([O:34][C:35]3[CH:36]=[CH:37][C:38]([C:41]#[N:42])=[CH:39][CH:40]=3)[CH:31]=[C:20]([O:21][C:22]3[CH:30]=[CH:29][C:25]([C:49](=[O:62])[NH2:44])=[CH:24][CH:23]=3)[CH:19]=2)[CH2:13][CH2:14]1)([CH3:53])([CH3:52])[CH3:51]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 9920397Tert-butyl ChloroformateHCID 66818525HCID 66818525, compound

Product 1

HCID 66818714HCID 66818714, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

0.6 g (1.05 mmol) of 4-[3-(4-tert-butoxycarbonylamino-cyclohexylcarbamoyl)-5-(4-cyano-phenoxy)-phenoxy]-benzoic acid was dissolved in 15 ml of THF. At −10° C. 0.18 ml (1.57 mmol) of N-methylmorpholine was added. The reaction mixture was stirred for 15 min at 0° C. 0.14 ml (1.36 mmol) of tert-butylchloroformate was added and the reaction mixture was stirred for 1 h at RT. Further 6.0 ml of 30% of ammonia solution was added during 10 min at 0° C. and reaction progress was monitored by TLC. Upon completion of the reaction the contents were diluted with 50 ml ethyl acetate. Organic layer was separated and Washed with 3×50 ml saturated sodium bicarbonate solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 0.4 g of the required product. Percentage purity (LCMS): 60.0%, (M+1)=570.2.

Workup

  1. customAt −10° C
  2. stirringthe reaction mixture was stirred for 1 h at RT
  3. customreaction progress
  4. customUpon completion of the reaction the contents
  5. customOrganic layer was separated
  6. washWashed with 3×50 ml saturated sodium bicarbonate solution
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3aa63d7aabee4dd6863ca63151fe263b
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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