5-Bromofuran-3-carboxamide → [5-(4-Carbamoyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

HRID 1783933Notes

Reaction equation

HRID 1783933 reaction equation
[C:1]([O:5][C:6](=[O:42])[N:7]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1)[C:8]1[C:9]2[N:10]([N:27]=[CH:28][N:29]=2)[C:11]([Sn](CCCC)(CCCC)CCCC)=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:44]1[O:48][CH:47]=[C:46]([C:49]([NH2:51])=[O:50])[CH:45]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH3:7].[C:1]([O:5][C:6](=[O:42])[N:7]([C:8]1[C:9]2[N:10]([N:27]=[CH:28][N:29]=2)[C:11]([C:44]2[O:48][CH:47]=[C:46]([C:49](=[O:50])[NH2:51])[CH:45]=2)=[CH:12][N:13]=1)[C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 2

HCID 108214945-Bromofuran-3-carboxamideHCID 67047357(4-Morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester

Product 2

HCID 222AmmoniaHCID 67047322[5-(4-Carbamoyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl esterYield 65.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

This compound may be prepared using methods as described for Compound 35, step 3 using (4-morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (137 mg, 0.199 mmol), 5-bromo-furan-3-carboxamide (76 mg, 0.4 mmol) and Pd(PPh3)4 (23 mg, 0.020 mmol) in DMF (1 mL). Purification of the reaction mixture eluting with 98:2 DCM:MeOH and 96:4 DCM:NH3 (7M in MeOH) affords the title compound (33 mg, 33%).

Workup

  1. customThis compound may be prepared
  2. customPurification of the reaction mixture
  3. washeluting with 98:2 DCM

Sources & evidence

ORD record
ord-4682667b785a4aff8b0f28ad39cf080c
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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