Potassium Carbonate → (S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

HRID 2280160Notes

Reaction equation

HRID 2280160 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH:8][C:9](=[O:20])OC2C=CC([N+]([O-])=O)=CC=2)=[CH:3][CH:2]=1.Cl.[NH2:22][C:23]1[C:24]2[C:34]([O:35][CH2:36][C@H:37]3[CH2:42][CH2:41][CH2:40][NH2+:39][CH2:38]3)=[CH:33][CH:32]=[CH:31][C:25]=2[NH:26][S:27](=[O:30])(=[O:29])[N:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:22][C:23]1[C:24]2[C:34]([O:35][CH2:36][C@H:37]3[CH2:42][CH2:41][CH2:40][N:39]([C:9]([NH:8][CH2:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:20])[CH2:38]3)=[CH:33][CH:32]=[CH:31][C:25]=2[NH:26][S:27](=[O:29])(=[O:30])[N:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86714280(S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochlorideHCID 867143034-Nitrophenyl pyridin-4-ylmethylcarbamate

Product 1

HCID 73213731(S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-nitrophenyl (pyridin-4-ylmethyl)carbamate (Example 27d, 27.3 mg, 100 umol), (S)-3-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochloride (Example 2a, 34.6 mg, 0.10 mmol) and K2CO3 in DMF (1 mL) was stirred at room temperature overnight. The resulting mixture was filtered and purified by preparative HPLC (10-90% acetonitrile in water) to provide the title product as a white solid. MS=445 (MH+).

Workup

  1. filtrationThe resulting mixture was filtered
  2. custompurified by preparative HPLC (10-90% acetonitrile in water)

Sources & evidence

ORD record
ord-8031dac2980f47988f39d3e4a61ed05b
Source dataset
uspto-grants-2015_09
Patent number
US09138013B2

Reaction notes

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