Aniline → HCID 15051732, compound

HRID 236590Notes

Reaction equation

HRID 236590 reaction equation
C(=O)(OCC1C2(O)ON(CC3C2N3)C2C1=C(O)C=C(C=O)C=2)N.NC1C=CC=CC=1.[C:31](=[O:59])([O:33][CH2:34][CH:35]1[C:47]2([OH:49])[O:48][N:42]([CH2:43][CH:44]3[CH:46]2[NH:45]3)[C:41]2[C:36]1=[C:37]([OH:58])[CH:38]=[C:39]([CH:50]=[N:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH:40]=2)[NH2:32]>CO.[Pd]>[C:31](=[O:59])([O:33][CH2:34][CH:35]1[C:47]2([OH:49])[O:48][N:42]([CH2:43][CH:44]3[CH:46]2[NH:45]3)[C:41]2[C:36]1=[C:37]([OH:58])[CH:38]=[C:39]([CH2:50][NH:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[CH:40]=2)[NH2:32]

Participants

6

Reactant 3

HCID 6115AnilineHCID 10448726(4-Formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-trien-8-yl)methyl carbamateHCID 86741320HCID 86741320, compound

Product 1

HCID 15051732HCID 15051732, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]-tetradeca-2,4,6-trien-8-ylmethyl carbamate (50 mg) was dissolved in methanol (5 ml). Aniline (0.05 ml) was added to this solution and the mixture was allowed to stand at room temperature for 3 hours to give a solution containing 6,9-dihydroxy-4-phenyliminomethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate. 10% Palladium on carbon (100 mg) was added to the solution, and the mixture was stirred for 2 hours at room temperature under hydrogen atmosphere (4.5 atm). The mixture was filtered through cellulose powder and the filter cake was washed with methanol (20 ml). The filtrate and the washings were combined and evaporated in vacuo. The residue was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform, methanol and water (65:25:4, v/v/v) to afford 4-anilinomethyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (25 mg).

Workup

  1. customto give a solution
  2. filtrationThe mixture was filtered through cellulose powder
  3. washthe filter cake was washed with methanol (20 ml)
  4. customevaporated in vacuo
  5. additionwas developed with a mixture of chloroform, methanol and water (65:25:4, v/v/v)

Sources & evidence

ORD record
ord-4993ecb9e94a4ab2acdb552699aaf6c1
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

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