1,4-Dioxa-8-azaspiro(4.5)decane → (1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

HRID 2241675Notes

Reaction equation

HRID 2241675 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([OH:23])=O)=[CH:15]3)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C1(N2CCN(C(C3C=C4C(=CC=3)NC(C(N3CCS(=O)(=O)CC3)=O)=C4)=O)CC2)CCCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[O:78]1[C:82]2([CH2:87][CH2:86][NH:85][CH2:84][CH2:83]2)[O:81][CH2:80][CH2:79]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[O:78]1[C:82]2([CH2:87][CH2:86][N:85]([C:21]([C:16]3[NH:17][C:18]4[C:14]([CH:15]=3)=[CH:13][C:12]([C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][CH2:6]3)=[O:11])=[CH:20][CH:19]=4)=[O:23])[CH2:84][CH2:83]2)[O:81][CH2:80][CH2:79]1

Participants

7

Reactant 5

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 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 68684152(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanoneYield 64%

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 hydrochlorid (example 1, intermediate b), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (commercially available), 1,4-dioxa-8-azaspiro[4.5]decane (commercially available) and N,N-diisopropylethylamine in N,N-dimethylformamide, to give the desired product as a light brown solid (64%).

Sources & evidence

ORD record
ord-8ccb6a8daf7746998301dda103efc61a
Source dataset
uspto-grants-2010_05
Patent number
US07723325B2

Reaction notes

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