Cyclopentanol → HCID 68190291, compound

HRID 513782Notes

Reaction equation

HRID 513782 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:13](=[C:14]3[C:19]=1[CH:18]=[CH:17][CH:16]=[N:15]3)[NH:12][S:11](=[O:21])(=[O:20])[C:10]1[C:5]2=[CH:6][C:7]([C:22]([OH:24])=[O:23])=[CH:8][CH:9]=1.[CH:25]1(O)[CH2:29][CH2:28][CH2:27][CH2:26]1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH:25]1([O:23][C:22]([C:7]2[CH:6]=[C:5]3[C:10]([S:11](=[O:21])(=[O:20])[NH:12][C:13]4[C:4]3=[CH:3][C:2]([Cl:1])=[C:19]3[C:14]=4[N:15]=[CH:16][CH:17]=[CH:18]3)=[CH:9][CH:8]=2)=[O:24])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 7298CyclopentanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68190302HCID 68190302, compound

Product 1

HCID 68190291HCID 68190291, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

In a similar fashion using route 54 general procedure 123, 12-chloro-6,6-dioxo-5,6-dihydro-6λ*6*-thia-4,5-diaza-chrysene-9-carboxylic acid 524 (150 mg, 0.41 mmol), cyclopentanol (0.19 ml, 2.0 mmol), EDC.HCl (88 mg, 0.45 mmol), DMAP (6 mg, 0.04 mmol) and DMF (1 ml) gave the title compound (50 mg, 28%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-b01ed8a202d040ada4f61a23245f7e9c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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