1-Amino-4-methylpiperazine → 4',9,9'-trihydroxy-6'-methoxy-3-[[(4-methylpiperazin-1-yl)hydrazinylidene]methyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[g]naphthalene]-1,1',3',5',8'-pentone

HRID 887684Notes

Reaction equation

HRID 887684 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.[NH2:38][N:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1.C1C=CC(C[NH:53]C(CN2C3C(=CC=CC=3)C(C=O)=C2)=O)=CC=1>CN(C=O)C.FC(F)(F)C(O)=O>[CH3:45][N:42]1[CH2:43][CH2:44][N:39]([NH:38][N:53]=[CH:35][C:27]2[NH:28][C:29](=[O:34])[C:30]3[C:25]([CH:26]=2)=[CH:24][C:23]2[CH2:22][CH2:21][C:18]4([C:17](=[O:37])[C:4]5=[C:5]([OH:16])[C:6]6[C:7](=[O:15])[CH:8]=[C:9]([O:13][CH3:14])[C:10](=[O:12])[C:11]=6[C:2]([OH:1])=[C:3]5[C:19]4=[O:20])[C:32]=2[C:31]=3[OH:33])[CH2:40][CH2:41]1

Participants

6

Reactant 3

HCID 813491-Amino-4-methylpiperazineHCID 892769Aldehyde resinHCID 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 1784933284',9,9'-trihydroxy-6'-methoxy-3-[[(4-methylpiperazin-1-yl)hydrazinylidene]methyl]spiro[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) mg (9.42 μmol) fredericamycin aldehyde (4) are dissolved in 500 μl DMF and 25 μl trifluoracetic acid. At room temperature, 1.30 mg (11.3 μmol) 1-amino-4-methyl-piperazine is added. After stirring for 4.5 h at room temperature, 1 equivalent each of Wang aldehyde resin and sulfonohydrazide resin is added and stirred for 2 h.

Workup

  1. stirringstirred for 2 h.

Sources & evidence

ORD record
ord-0d9dc9f5c05a4e5695b918cc8efa750d
Source dataset
uspto-grants-2012_08
Patent number
US08247424B2

Reaction notes

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