2-Morpholinoethylamine → HCID 178427950, compound

HRID 2218414Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14](F)=[C:13]([N+:18]([O-])=O)[CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[N:22]1([CH2:28][CH2:29][NH2:30])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>>[Cl:1][C:2]1[C:3]([CH3:21])=[C:4]2[N:10]=[C:9]([C:11]3[CH:12]=[C:13]([NH2:18])[C:14]([NH:30][CH2:29][CH2:28][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:15][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

Reactant 2

HCID 4082852-Morpholinoethylamine

HCID 178427944HCID 178427944, compound

Product 1

HCID 178427950HCID 178427950, compound

Conditions

Temperature: 180 °C

Procedure

5-Chloro-4-methylpyridine-2,3-diamine (Example 249b) (1.47 g, 9 mmol) and 4-fluoro-3-nitrobenzoic acid (1.73 g, 9 mmol) were mixed in phosphorous oxychloride (50 ml) and heated to 110° C. for 64 h. When cool, the excess phosphorous oxychloride was removed in vacuo to afford a brown semi-solid (about 4 g) consisting of 6-chloro-2-(4-fluoro-3-nitrophenyl)-7-methyl-3H-imidazo[4,5-b]pyridine and various inorganic material. To 1.0 g of this crude material, (2-morpholin-4-ylethyl)amine (2 ml) was added and the mixture heated in the microwave oven (180° C., 20 min).

Sources & evidence

ORD record: ord-2381ca2f0dba415e9d686a53196e4bab
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410966B2

Reaction notes

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