Aldehyde resin → 3-[(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]-4',9,9'-trihydroxy-6'-methoxyspiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[g]naphthalene]-1,1',3',5',8'-pentone

HRID 887685Notes

Reaction equation

HRID 887685 reaction equation
[OH:1][C:2]1[C:11]2[C:10](=[O:12])[C:9]([O:13][CH3:14])=[CH:8][C:7](=[O:15])[C:6]=2[C:5]([OH:16])=[C:4]2[C:17](=[O:37])[C@:18]3([C:32]4[C:31]([OH:33])=[C:30]5[C:25]([CH:26]=[C:27]([CH:35]=O)[NH:28][C:29]5=[O:34])=[CH:24][C:23]=4[CH2:22][CH2:21]3)[C:19](=[O:20])[C:3]=12.Br.[NH:39]([C:41]1[NH:42][CH2:43][CH2:44][N:45]=1)[NH2:40].C1C=CC(CNC(CN2C3C(=CC=CC=3)C(C=O)=C2)=O)=CC=1>CN(C=O)C.FC(F)(F)C(O)=O>[NH:45]1[CH2:44][CH2:43][N:42]=[C:41]1[NH:39][N:40]=[CH:35][C:27]1[NH:28][C:29](=[O:34])[C:30]2[C:25]([CH:26]=1)=[CH:24][C:23]1[CH2:22][CH2:21][C:18]3([C:17](=[O:37])[C:4]4=[C:5]([OH:16])[C:6]5[C:7](=[O:15])[CH:8]=[C:9]([O:13][CH3:14])[C:10](=[O:12])[C:11]=5[C:2]([OH:1])=[C:3]4[C:19]3=[O:20])[C:32]=1[C:31]=2[OH:33]

Participants

6

Reactant 3

HCID 892769Aldehyde resinHCID 30850992-Hydrazino-delta-2-imidazoline hydrobromideHCID 178493334(8S)-4',9,9'-trihydroxy-6'-methoxy-1,1',3',5',8'-pentaoxospiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-3-carbaldehyde

Product 1

HCID 1784933273-[(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]-4',9,9'-trihydroxy-6'-methoxyspiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[g]naphthalene]-1,1',3',5',8'-pentone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Five (5.00) mg (9.42 μmol) fredericamycin aldehyde (4) are dissolved in 500 μl DMF and 25 μl trifluoracetic acid. At room temperature, 2.05 mg (11.3 μmol) 2-hydrazino-2-imidazolin hydrobromide is added. After stirring for 4.5 h at room temperature, 1 equivalent each of Wang aldehyde resin and sulfonohydrazide resin are added and stirred for 2 h. Separation of the resin by filtration and concentration of the reaction solution at high vacuum.

Workup

  1. stirringstirred for 2 h
  2. customSeparation of the resin
  3. filtrationby filtration and concentration of the reaction solution at high vacuum

Sources & evidence

ORD record
ord-d2ce06a2d1c54918b99a142272e17fa2
Source dataset
uspto-grants-2012_08
Patent number
US08247424B2

Reaction notes

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