Diisopropylethylamine → HCID 86726648, compound

HRID 1499391Notes

Reaction equation

HRID 1499391 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH:15]1[CH2:20][CH2:19][CH2:18][C@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:16]1.CCN(C(C)C)C(C)C>C(O)CCC>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[N:15]1[CH2:20][CH2:19][CH2:18][C@H:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:16]1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 86726648HCID 86726648, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a 5 mL microwave vial containing 4-chloro-3-nitroquinoline (Ark Pharm, 312.9 mg, 1.500 mmol) and tert-butyl (3S)-piperidin-3-ylcarbamate (Combi-Blocks, 358.9 mg, 1.792 mmol), 1-butanol (3.00 mL) was added followed by DIPEA (405.1 mg, 3.134 mmol). The reaction mixture was heated at 100° C. under microwave irradiation for 2 h. The reaction was then concentrated under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a yellow oil (293.5 mg, 53%). LCMS calc. for C19H25N4O4 (M+H)+: m/z=373.2. found 373.2.

Workup

  1. additionwas added
  2. concentrationThe reaction was then concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-09bc4056f3c34d409d815df1290c4c45
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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