Diisopropylethylamine → HCID 86615807, compound

HRID 1820417Notes

Reaction equation

HRID 1820417 reaction equation
C(N1CCN(C(C2C=C3C(=CC=2)NC(C(O)=O)=C3)=O)CC1)(C)C.[CH:24]1([N:29]2[CH2:34][CH2:33][N:32]([C:35]([C:37]3[CH:38]=[C:39]4[C:43](=[CH:44][CH:45]=3)[NH:42][C:41]([C:46]([N:48]3[CH2:53]CS(=O)(=O)CC3)=[O:47])=[CH:40]4)=[O:36])[CH2:31][CH2:30]2)[CH2:28]CC[CH2:25]1.[F:56][C:57]1(NC)[CH2:60][O:59][CH2:58]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:56][C:57]1([CH2:53][NH:48][C:46]([C:41]2[NH:42][C:43]3[C:39]([CH:40]=2)=[CH:38][C:37]([C:35]([N:32]2[CH2:33][CH2:34][N:29]([CH:24]([CH3:25])[CH3:28])[CH2:30][CH2:31]2)=[O:36])=[CH:45][CH:44]=3)=[O:47])[CH2:60][O:59][CH2:58]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67318981HCID 67318981, compoundHCID 685341205-(4-isopropyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acidHCID 68680722[5-(4-Cyclopentyl-piperazine-1-carbonyl)-1H-indol-2-yl]-(1,1-dioxo-thiomorpholin-4-yl)-methanone2×

Product 1

HCID 86615807HCID 86615807, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 1, from 5-(4-isopropyl-piperazine-1-carbonyl)-1H-indole-2-carboxylic acid 1:1 hydrochloride (example 1, intermediate b), (3-fluoro-oxetan-3-yl)-methylamine (commercially available), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available) and N,N-diisopropylethylamine in N,N-dimethylformamide, to give the desired product as a colorless solid (42%).

Sources & evidence

ORD record
ord-091f3261fe854af4a325b5171d0f1fb1
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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