Ammonia → HCID 178513915, compound

HRID 632945Notes

Reaction equation

HRID 632945 reaction equation
[C:1]1([C:7]2[O:8][C:9]([C:36]([F:39])([F:38])[F:37])=[C:10]([C:12]([NH:14][CH2:15][CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C@H:26]4[CH2:31][CH2:30][C@H:29]([CH2:32][C:33]([OH:35])=O)[CH2:28][CH2:27]4)=[CH:22][CH:21]=3)=[O:18])=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(OC(C)C)=O.C([N:49](CC)CC)C.N>O1CCOCC1.O.C(OCC)(=O)C.CN(C=O)C.C(Cl)Cl>[C:33]([CH2:32][C@H:29]1[CH2:30][CH2:31][C@H:26]([C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:17]([CH2:16][CH2:15][NH:14][C:12]([C:10]3[N:11]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:8][C:9]=3[C:36]([F:39])([F:38])[F:37])=[O:13])=[O:18])=[CH:25][CH:24]=2)[CH2:27][CH2:28]1)(=[O:35])[NH2:49]

Participants

10

Reactant 4

HCID 222AmmoniaHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 178525557HCID 178525557, compound

Product 1

HCID 178513915HCID 178513915, compoundYield 100.1%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Trans-[4-(4-{3-[(2-phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionylamino}phenyl)cyclohexyl]acetic acid (41 mg, 0.07 mmol) was added to DCM (4 mL) and DMF (1 mL) solution. Isopropyl chloroformate (0.02 mL, 0.11 mmol) and triethyl amine (0.2 mL, 0.15 mmol) were added dropwise thereto at 0° C., a temperature of the product was raised to room temperature, and stirred for 2 hours. Then, 0.5 M ammonia dissolved in 1,4-dioxane was added and stirred for 2 hours. Ethyl acetate (20 mL) and water (40 mL) were added to the reaction mixture. Then, the organic layer was separated and the product was dried with anhydrous sodium sulfate to prepare a solid under reduced pressure. The product was purified by chromatography using methanol/DCM 2-10% to obtain the desired compound (38 mg, 93%) as a white solid.

Workup

  1. additionwas added
  2. stirringstirred for 2 hours
  3. customThen, the organic layer was separated
  4. dry with materialthe product was dried with anhydrous sodium sulfate
  5. customto prepare a solid under reduced pressure
  6. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-16254e996d6f462192efc285c952032c
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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