Diisopropylethylamine → HCID 90046331, compound

HRID 1507596Notes

Reaction equation

HRID 1507596 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:20])([CH3:19])[C:7](=[O:18])[N:8]2[CH2:11][CH2:12][CH2:13][S:14][CH:15]2[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>ClCCl>[CH:15]1([S:14][CH2:13][CH2:12][CH2:11][N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:21](=[O:28])[C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)[CH:10]=3)[C:6]([CH3:20])([CH3:19])[C:7]2=[O:18])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 417436Pyridine-4-carbonyl chlorideHCID 90046302HCID 90046302, compound

Product 1

HCID 90046331HCID 90046331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-amino-1-(3-(cyclopropylthio)propyl)-3,3-dimethylindolin-2-one (160 mg, 496 μmol), isonicotinoyl chloride (84.2 mg, 595 μmol) and DIPEA (192 mg, 260 μl, 1.49 mmol) in dichloromethane (3 ml) was stirred at room temperature for 3 hours. The crude material was purified by flash chromatography on silica gel using EtOAc/heptane as eluent. The title compound was obtained as yellow viscous oil (131 mg).

Workup

  1. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-244d7a2b439a4939ab71138e3bab83b9
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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