4-(6-Chloropyridine-3-carbonyl)morpholine → HCID 44198081, compound

HRID 1969111Notes

Reaction equation

HRID 1969111 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([CH:28]=[CH:29][N:30]=2)[CH:5]=[C:6]([C:8]2[C:9]([CH3:27])=[C:10]([NH:14][C:15](=[O:26])[C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=3)[CH:11]=[CH:12][CH:13]=2)[CH:7]=1.Cl[C:32]1[N:37]=[CH:36][C:35]([C:38]([N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)=[O:39])=[CH:34][CH:33]=1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:6]3[CH:7]=[C:2]([NH:1][C:32]4[CH:33]=[CH:34][C:35]([C:38]([N:40]5[CH2:41][CH2:42][O:43][CH2:44][CH2:45]5)=[O:39])=[CH:36][N:37]=4)[C:3]4[N:4]([CH:28]=[CH:29][N:30]=4)[CH:5]=3)[C:9]=2[CH3:27])=[O:26])=[CH:17][CH:18]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 4

HCID 8574994-(6-Chloropyridine-3-carbonyl)morpholineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 42643655HCID 42643655, compound

Product 1

HCID 44198081HCID 44198081, compound

Conditions

Temperature
200 °C

Procedure

A mixture of N-[3-(8-Amino-imidazo[1,2-a]pyridin-6-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide (0.69 g, 1.73 mmol), (6-Chloro-pyridin-3-yl)-morpholin-4-yl-methanone (1.17 g, 5.19 mmol), sodium t-butoxide (0.23 g, 2.42 mmol), Pd(II)acetate (19 mg, 0.08 mmol) and 2-(dicyclohexyl-phosphino)biphenyl was stirred at 200° C. in a microwave for 100 min.

Sources & evidence

ORD record
ord-787db149e50c45aa83fbd2550ed16cc8
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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