Ammonia → HCID 54754845, compound

HRID 2089177Notes

Reaction equation

HRID 2089177 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:9]=2)[C:4]([NH:15][CH2:16][C:17]([NH:19][CH:20]2[CH2:23][N:22]([CH:24]3[CH2:29][CH2:28][CH:27]([C:30](O)=[O:31])[CH2:26][CH2:25]3)[CH2:21]2)=[O:18])=[N:3]1.CC[N:35]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N>C1COCC1.C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:9]=2)[C:4]([NH:15][CH2:16][C:17]([NH:19][CH:20]2[CH2:21][N:22]([CH:24]3[CH2:29][CH2:28][CH:27]([C:30]([NH2:35])=[O:31])[CH2:26][CH2:25]3)[CH2:23]2)=[O:18])=[N:3]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 56661559HCID 56661559, compound

Product 1

HCID 54754845HCID 54754845, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-{3-[2-(1-Methyl-5-trifluoromethyl-1H-indazol-3-ylamino)-acetylamino]-azetidin-1-yl}-cyclohexane carboxylic acid (as prepared in the previous step, 100 mg, 0.22 mmol), EDCI (Aldrich, 65 mg, 0.33 mmol), HOBt (Aldrich, 45 mg, 0.33 mmol) and ammonia in THF (1N, Aldrich, 0.5 mL) in DCM (5 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel column chromatography using DCM: 7N NH3 in MeOH (10:1) as eluent to give the title compound as white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a616e1b0ec354422862503c9206a4498
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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