Ammonia → HCID 22353160, compound

HRID 895349Notes

Reaction equation

O.C[O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([N:29]2[CH2:34][CH2:33][N:32]([CH2:35][C:36]([OH:38])=[O:37])[CH2:31][CH2:30]2)[CH2:12][O:13][CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)=[CH:7][CH:6]=1.FC(C1C=C(C=C(C(F)(F)F)C=1)COCC(C1C=CC(C(OC)=O)=CC=1)[N:51]1CCN(CC(O)=O)CC1)(F)F.N>CO>[F:28][C:25]([F:26])([F:27])[C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:18]=1)[CH2:14][O:13][CH2:12][CH:11]([N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]([OH:38])=[O:37])[CH2:31][CH2:30]1)[C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:3])[NH2:51])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a small autoclave, 1.5 g (2.73 mmoles) of 4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-(4-carboxymethyl-piperazin-1-yl)-ethyl]-benzoic acid methyl ester (compound 318) were dissolved in methanol. The solution was saturated with NH3 and heated at 100° C. for three days. Methanol was then evaporated and the crude product was purified by chromatography (eluent: CH2Cl2/MeOH/NH3: 80/20/0.5 v/v/v) to give 880 mg of {4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-(4-carbamoyl-phenyl)-ethyl]-piperazin-1-yl}-acetic acid (compound 321) as a grey solid. 4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-(4-carbamoylmethyl-piperazin-1-yl)-ethyl]-benzamide (compound 322) was isolated as a side product (150 mg).

Workup

customMethanol was then evaporated
customthe crude product was purified by chromatography (eluent: CH2Cl2/MeOH/NH3: 80/20/0.5 v/v/v)

Sources & evidence

ORD record: ord-0add83af1ab6499b86a29f6072c2d9c3
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916797B2

Reaction notes

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