1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine → tert-butyl 3-(cyanomethyl)-3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

HRID 1853024Notes

Reaction equation

HRID 1853024 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[N:14]=[C:13]([C:15]3[CH:16]=[N:17][NH:18][CH:19]=3)[N:12]3[CH:20]=[CH:21][N:22]=[C:11]3[CH:10]=2)[CH:6]=[N:5]1)([CH3:3])[CH3:2].[C:23]([CH:25]=[C:26]1[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27]1)#[N:24]>>[C:23]([CH2:25][C:26]1([N:17]2[CH:16]=[C:15]([C:13]3[N:12]4[CH:20]=[CH:21][N:22]=[C:11]4[CH:10]=[C:9]([C:7]4[CH:6]=[N:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:8]=4)[N:14]=3)[CH:19]=[N:18]2)[CH2:29][N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:27]1)#[N:24]

Participants

3

Reactant 2

HCID 457892161-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidineHCID 674577627-(1-isopropyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

Product 1

HCID 67456728tert-butyl 3-(cyanomethyl)-3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylateYield 64%

Procedure

7-(1-isopropyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Example 34, Step B) was reacted in the same manner as Example 34, Step C, replacing 3-cyclopropylacrylonitrile with tert-butyl 3-(cyanomethylene)azetidine-1-carboxylate (Preparation F, Step A) to obtain tert-butyl 3-(cyanomethyl)-3-(4-(7-(1-isopropyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (0.090 g, 0.1846 mmol, 64% yield). MS (apci) m/z=488.3 (M+H).

Sources & evidence

ORD record
ord-70fc4a528f73469a8a414cedfafceb92
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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