1-Hydroxybenzotriazole → HCID 68190304, compound

HRID 513783Notes

Reaction equation

HRID 513783 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.[C:25]([N:32]1[CH2:37][CH2:36][CH:35](O)[CH2:34][CH2:33]1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[C:28]([O:27][C:25]([N:32]1[CH2:37][CH2:36][CH:35]([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])[CH2:34][CH2:33]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68190302HCID 68190302, compound

Product 1

HCID 68190304HCID 68190304, compoundYield 47.7%

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), 1-Boc-4-piperidinol (0.11 g, 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 (70 mg, 46%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-9feb58bb81dd4b7d89bb3beb13e0754c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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