Triethylamine → HCID 68418947, compound

HRID 1765066Notes

Reaction equation

HRID 1765066 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[N:11][C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=3)=[N:9]2)[CH:5]=[CH:4][N:3]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][C@H:33]([NH2:37])[CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].S(C1C=CC(NC2N=CN(C3C=CN=C(N[C@H]4CCCNC4)C=3)N=2)=CC=1)(=O)(=O)N.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.CN1C(=O)CCC1.ClCCl>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][C@H:33]([NH:37][C:2]2[CH:7]=[C:6]([N:8]3[CH:12]=[N:11][C:10]([NH:13][C:14]4[CH:19]=[CH:18][C:17]([S:20](=[O:22])(=[O:21])[NH2:23])=[CH:16][CH:15]=4)=[N:9]3)[CH:5]=[CH:4][N:3]=2)[CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 21106446HCID 21106446, compoundHCID 58883330HCID 58883330, compound

Product 1

HCID 68418947HCID 68418947, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A microwave reaction vessel was charged with 50 mg of 4-[1-(2-Chloro-pyridin-4-yl)-1H-[1,2,4]triazol-3-ylamino]-benzenesulfonamide (0.14 mmol, 1 equiv), 110 mg (S)-3-amino-piperidine-1-carboxylic acid tert-butyl ester (0.57 mmol, 4 equiv) and 17.0 mg DMAP (0.014 mmol, 0.1 equiv) in NMP (1.5 mL). The resulting solution was warmed to 130° C. via microwave irradiation for 20 min and then heated at 180° C. for an additional 70 min via microwave irradiation. The reaction mixture was cooled and concentrated in vacuo and the residue purified by preparative HPLC. To a solution of 12.0 mg of this product, 3-(S)-{4-[3-(4-sulfamoyl-phenylamino)-[1,2,4]triazol-1-yl]-pyridin-2-ylamino}-piperidine (0.029 mmol, 1 equiv) in dichloromethane (5 mL), di-tert-butyl dicarbonate (9.5 mg, 0.043 mmol, 1.5 equiv) and 6 μL triethylamine (0.058 mmol, 2 equiv) were added and the resulting solution stirred at rt for 1 h. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography on silica gel eluting with 50% EtOAc: petroleum ether moving to EtOAc (4.2 mg, 29%); MS (ES+) m/e 515.55, (ES−) m/e 513.70

Workup

  1. customA microwave reaction vessel
  2. temperatureheated at 180° C. for an additional 70 min via microwave irradiation
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by preparative HPLC
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customthe residue purified by column chromatography on silica gel eluting with 50% EtOAc

Sources & evidence

ORD record
ord-dda7a30fef2a4cf0ae71a6097e8efc9c
Source dataset
uspto-grants-2007_06
Patent number
US07226920B2

Reaction notes

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