Imidazole → HCID 68837072, compound

HRID 2112959Notes

Reaction equation

C(O[C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8]([C:22]2[CH:23]=[N:24][C:25]([N:28]([CH3:30])[CH3:29])=[N:26][CH:27]=2)[CH:7]=1)=[O:5])C.C(OC(C1[N:41]2C=C(NC(NC(C)C)=O)N=[C:40]2[CH:39]=C(C2C=NC(N(C)C)=NC=2)C=1)=O)C.N1C=CN=C1>C(N)C.O>[CH2:40]([NH:41][C:4]([C:6]1[N:11]2[N:12]=[C:13]([NH:15][C:16]([NH:18][CH:19]([CH3:20])[CH3:21])=[O:17])[N:14]=[C:10]2[CH:9]=[C:8]([C:22]2[CH:23]=[N:24][C:25]([N:28]([CH3:29])[CH3:30])=[N:26][CH:27]=2)[CH:7]=1)=[O:5])[CH3:39]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of the product of Example 116, 7-(2-dimethylamino-pyrimidin-5-yl)-2-(3-isopropyl-ureido)-imidazo[1,2-a]pyridine-5-carboxylic acid ethyl ester (0.149 g, 0.361 mmol) in ethylamine (2 mL of a 70% aqueous solution) was treated with imidazole (2 g) and heated to 100° C. for 1 min until it became a homogeneous solution. The reaction was cooled to 23° C. and diluted with water (15 mL). The precipitated solid was collected by vacuum filtration then dried in vacuo to give 7-(2-dimethylamino-pyrimidin-5-yl)-2-(3-isopropyl-ureido)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid ethylamide. MS (APCI+)=412.2

Workup

temperatureThe reaction was cooled to 23° C.
filtrationThe precipitated solid was collected by vacuum filtration
customthen dried in vacuo

Sources & evidence

ORD record: ord-33fcb65657c346bf9eaa4fcdaf955444
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524860B2

Reaction notes

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