Azetidine → HCID 178522279, compound

HRID 1958318Notes

Reaction equation

HRID 1958318 reaction equation
C([N:4]([CH:7]([CH3:9])C)[CH2:5]C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:32]1([C:38]2[N:39]=[C:40]3[N:45]=[C:44]([NH:46][C:47]([C:49]4[N:53]=[N:52][NH:51][C:50]=4[C:54]([OH:56])=O)=[O:48])[CH:43]=[CH:42][N:41]3[CH:57]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N1CCC1>CN(C=O)C.O.CC#N>[C:32]1([C:38]2[N:39]=[C:40]3[N:45]=[C:44]([NH:46][C:47]([C:49]4[N:53]=[N:52][NH:51][C:50]=4[C:54]([N:4]4[CH2:5][CH2:9][CH2:7]4)=[O:56])=[O:48])[CH:43]=[CH:42][N:41]3[CH:57]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178522280HCID 178522280, compound

Product 1

HCID 178522279HCID 178522279, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent5×

Procedure

Diisopropylethylamine (89 mg, 0.69 mmol) and TBTU (88 mg, 0.27 mmol) were added to a solution of 5-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-3H-[1,2,3]triazole-4-carboxylic acid (80 mg, 0.23 mmol) in DMF (1 ml), and the dark brown solution was stirred for 30 min at RT. Azetidine (39 mg, 0.68 mmol) was added, and the mixture was stirred at RT overnight. The title compound (25 mg, 28%) was obtained from the reaction mixture by preparative HPLC (254 nm, Agilent Zorbax XdB-C18, Run: 7 min, Flow: 30 ml/min, Gradient: 0.0 min: 95/5 H2O/CH3CN; 0.5 min: 95/5 H2O/CH3CN 4.5 min: 5/95 H2O/CH3CN; 6.9 min 5/95 H2O/CH3CN; 7 min 95/5 H2O/CH3CN). MS (m/e)=389.3 [M+H+].

Workup

  1. stirringthe mixture was stirred at RT overnight

Sources & evidence

ORD record
ord-65f25e5f889743e4ac602ee75b99a2dd
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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