Dichloromethane → 4-(Benzylamino)-6-{[4-(morpholinomethyl)phenyl]amino}pyridine-3-carboxyamide

HRID 2035520Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[CH:11][C:10]=1[CH2:16][C:17]([NH2:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.CC(C)([O-])C.[Na+].[O:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]2[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=2)[CH2:31][CH2:30]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:40][C:39]2[CH:38]=[CH:37][C:36]([CH2:35][N:32]3[CH2:31][CH2:30][O:29][CH2:34][CH2:33]3)=[CH:42][CH:41]=2)[N:12]=[CH:11][C:10]=1[CH2:16][C:17]([NH2:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

20 mg of 4-(benzylamino)-6-chloropyridine-3-carboxyamide (the compound of Example 1), 3.1 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II).methylene chloride adduct, 6.3 mg of 1,1′-bis (diphenylphosphino)ferrocene and 7.3 mg of sodium tert-butoxide were added to 1 mL of 1,4-dioxane, to which 18 mg of 4-(morpholinomethyl)aniline was added in an argon atmosphere, and stirred at 100° C. for 3 hours. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1) to obtain 9 mg (28%) of the title compound as a light yellow powder.

Workup

additionwas added in an argon atmosphere
customThe solvent was evaporated
customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record: ord-237041ba17ff4022b5a95bb656322f87
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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