1-(2-Furoyl)piperazine → 1-[4-(Furan-2-carbonyl)-piperazin-1-yl]-3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propan-1-one

HRID 220880Notes

Reaction equation

HRID 220880 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[CH:31]=[C:30]([C:32]([N:34]2[CH2:43][C:42]3[CH:41]=[N:40][N:39]([CH3:44])[C:38]=3[NH:37][C:36]3[CH:45]=[CH:46][CH:47]=[CH:48][C:35]2=3)=[O:33])[CH:29]=[CH:28][C:27]=1[CH2:49][CH2:50][C:51]([OH:53])=O.[O:54]1[CH:58]=[CH:57][CH:56]=[C:55]1[C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)=[O:60]>CN(C=O)C.CCN(C(C)C)C(C)C>[O:54]1[CH:58]=[CH:57][CH:56]=[C:55]1[C:59]([N:61]1[CH2:62][CH2:63][N:64]([C:51](=[O:53])[CH2:50][CH2:49][C:27]2[CH:28]=[CH:29][C:30]([C:32]([N:34]3[CH2:43][C:42]4[CH:41]=[N:40][N:39]([CH3:44])[C:38]=4[NH:37][C:36]4[CH:45]=[CH:46][CH:47]=[CH:48][C:35]3=4)=[O:33])=[CH:31][C:26]=2[CH3:25])[CH2:65][CH2:66]1)=[O:60]

Participants

6

Reactant 3

HCID 5502061-(2-Furoyl)piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1361283543-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionic Acid

Product 1

HCID 1361283861-[4-(Furan-2-carbonyl)-piperazin-1-yl]-3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propan-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of HBTU (1.90 mg, 0.005 mmol) in DMF (0.05 ml) was added to a solution of 3-[2-methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionic acid from Example E45 (1.95 mg, 0.005 mmol) in DMF (0.05 ml) and DIEA (0.0022 ml). The mixture was stirred at room temperature for 30 min then a solution of 1-(2-furoyl)piperazine (0.90 mg, 0.005 mmol) in DMF (0.05 ml) was added. The mixture was stirred for 18 h at room temperature then sol-vents were removed in vacuo to yield the title compound. (ESI)+: [M+H]+=553.4

Workup

  1. stirringThe mixture was stirred for 18 h at room temperature
  2. customthen sol-vents were removed in vacuo

Sources & evidence

ORD record
ord-e95be850b26c4b59a43cf0987adaec6b
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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