Citric Acid → HCID 10054740, compound

HRID 1394268Notes

Reaction equation

[CH3:1][N:2]([CH3:32])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:5][CH2:4]1.C(O)C.[C:36]([OH:48])(=[O:47])[CH2:37][C:38]([CH2:43][C:44]([OH:46])=[O:45])([C:40]([OH:42])=[O:41])[OH:39]>C(OCC)C>[C:36]([OH:48])(=[O:47])[CH2:37][C:38]([CH2:43][C:44]([OH:46])=[O:45])([C:40]([OH:42])=[O:41])[OH:39].[CH3:32][N:2]([CH3:1])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=3)[NH:18][CH:17]=2)=[O:12])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 40 °C

Procedure

The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(5-fluoro-1H-indol-3-yl)-ethyl]-urea (208 mg, 0.476 mmole) was dissolved in abs. ethanol (3.5 ml). The citric acid (92.5 mg, 0.481 mmole) was added in a single portion with stirring at approx. 40° C. After two hours' stirring at RT, no precipitate had formed. The reaction mixture was reduced to approx. 1 ml of solution and combined in portions with diethyl ether (20 ml). The resultant precipitate was filtered out after 1 h, washed with ether (3×3 ml) and dried under a vacuum. The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-[2-(5-fluoro-1H-indol-3-yl)-ethyl]-urea citrate (230 mg, 77%, Example 28) was a colorless solid.

Workup

stirringAfter two hours' stirring at RT
customno precipitate had formed
filtrationThe resultant precipitate was filtered out after 1 h
washwashed with ether (3×3 ml)
customdried under a vacuum

Sources & evidence

ORD record: ord-23de6273e5524fa68bf420e70c0cb650
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348354B2

Reaction notes

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