Diisopropylethylamine → HCID 59553212, compound

HRID 1641117Notes

Reaction equation

HRID 1641117 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][N:30]=1)[C:25](Cl)=[O:26].CCN(C(C)C)C(C)C>C1COCC1>[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][N:30]=1)[C:25]([NH:20][C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:12]=1)=[O:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 28000032-Chloropyridine-4-carbonyl chlorideHCID 110439124-(2-Morpholinoethoxy)naphthalen-1-amine

Product 1

HCID 59553212HCID 59553212, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-ylamine (1.38 g, 5.07 mmol), 2-chloroisonicotinoyl chloride (1.34 g, 7.6 mmol), DIPEA (1.81 ml, 10.1 mmol) and THF (30 ml) is stirred at room temperature for 12 hours. The mixture is quenched with water (100 ml). The crude product is extracted with EtOAc (2×50 ml), the combined organic layers are dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash column chromatography (3% MeOH in EtOAc) to afford 2-chloro-N-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-isonicotinamide (1.07 g, 51%). 1H NMR (DMSO-d6) δ 10.61 (s, 1H), 8.62 (d, 1H), 8.21 (d, 1H), 8.10 (s, 1H), 7.95 (m, 2H), 7.59 (d, 2H), 7.49 (d, 1H), 7.09 (d, 1H), 4.33 (m, 2H), 3.61 (m, 4H), 2.92 (m, 2H), 2.61 (m, 4H). MS: 412 (M+1).

Workup

  1. customThe mixture is quenched with water (100 ml)
  2. extractionThe crude product is extracted with EtOAc (2×50 ml)
  3. dry with materialthe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash column chromatography (3% MeOH in EtOAc)

Sources & evidence

ORD record
ord-14911ca8ecf54ee9a5b0d73f891e8c75
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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