Serinol → HCID 68190290, compound

HRID 513781Notes

Reaction equation

HRID 513781 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](O)=[O:23])=[CH:8][CH:9]=1.[NH2:25][CH:26]([CH2:29][OH:30])[CH2:27][OH:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[OH:28][CH2:27][CH:26]([NH:25][C:22]([C:7]1[CH:6]=[C:5]2[C:10]([S:11](=[O:20])(=[O:21])[NH:12][C:13]3[C:4]2=[CH:3][C:2]([Cl:1])=[C:19]2[C:14]=3[N:15]=[CH:16][CH:17]=[CH:18]2)=[CH:9][CH:8]=1)=[O:23])[CH2:29][OH:30]

Participants

6

Reactant 4

HCID 68294SerinolHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68190302HCID 68190302, compound

Product 1

HCID 68190290HCID 68190290, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 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 (100 mg, 0.27 mmol), serinol (50 mg, 0.55 mmol), EDC.HCl (80 mg, 0.41 mmol), HOBt (56 mg, 0.41 mmol), TEA (0.12 ml, 0.11 mmol) and DMF (1 ml) gave the title compound (40 mg, 33%) after purification by column chromatography with chloroform/MeOH (90:10) as the eluent.

Sources & evidence

ORD record
ord-8dada56286fd4d8694dc94c52f981ab0
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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