Dimethylformamide → HCID 22116938, compound

HRID 35946Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[C:6](=[O:7])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:4](=[O:20])[N:3]1[CH2:21][CH2:22][CH2:23][CH2:24][OH:25].[C:27](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.CN(C)C=O>CN(C)C1C=CN=CC=1.CCOCC.O>[O:20]=[C:4]1[N:3]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:2]([CH3:26])([CH3:1])[C:6](=[O:7])[N:5]1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:17])([F:18])[F:19])[CH:9]=1

Participants

Conditions

Temperature: 40 °C

Procedure

370 mg of the product of Example 58, 307 mg of trityl chloride in the presence of 10 mg of 4-dimethylamino-pyridine, 0.25 ml of triethylamine and 4 ml of dimethylformamide were stirred at ambient temperature for 16 hours. The mixture was heated to 40° C. for 4 hours, poured into water and extraction was carried out with ether. The extracts were washed with water and dried and the solvent was eliminated under reduced pressure. The residue was chromatographed on silica (eluant: cyclohexane--ethyl acetate 75-25) to obtain 467 mg of the expected product with a Rf=0.25.

Workup

washThe extracts were washed with water
customdried
customThe residue was chromatographed on silica (eluant: cyclohexane--ethyl acetate 75-25)

Sources & evidence

ORD record: ord-c07010a63ff843e696b77d4744466c6e
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411981

Reaction notes

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