5-Bromo-1,3-thiazole-2-carboxamide → 5-[8-(4-Morpholin-4-yl-phenylamino)-imidazo[1,2-a]pyrazin-5-yl]-thiazole-2-carboxylic acid amide

HRID 1924949Notes

Reaction equation

HRID 1924949 reaction equation
C(OC(=O)[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]([CH:27]=[CH:28][N:29]=2)[C:11]([Sn](CCCC)(CCCC)CCCC)=[CH:12][N:13]=1)(C)(C)C.Br[C:44]1[S:48][C:47]([C:49]([NH2:51])=[O:50])=[N:46][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>[N:36]1([C:33]2[CH:34]=[CH:35][C:30]([NH:7][C:8]3[C:9]4[N:10]([CH:27]=[CH:28][N:29]=4)[C:11]([C:44]4[S:48][C:47]([C:49]([NH2:51])=[O:50])=[N:46][CH:45]=4)=[CH:12][N:13]=3)=[CH:31][CH:32]=2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

5

Reactant 2

HCID 224972475-Bromo-1,3-thiazole-2-carboxamideHCID 59023110(4-Morpholin-4-yl-phenyl)-(5-tributylstannanyl-imidazo[1,2-a]pyrazin-8-yl)-carbamic acid tert-butyl ester

Product 1

HCID 573939925-[8-(4-Morpholin-4-yl-phenylamino)-imidazo[1,2-a]pyrazin-5-yl]-thiazole-2-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

In the same way as described for Compound 212, step 3, using (4-morpholin-4-yl-phenyl)-(5-tributylstannanyl-imidazo[1,2-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (0.25 g, 0.365 mmol), 5-bromo-thiazole-2-carboxylic acid amide (60.5 mg, 0.29 mmol) and Pd(PPh3)4 (63.3 mg, 0.055 mmol) in DMF. Purification by silica gel column chromatography eluting with 99:1 and 95:5 DCM:MeOH affords the title compound as a free base (27.4 mg, 49%).

Workup

  1. customPurification by silica gel column chromatography
  2. washeluting with 99:1 and 95:5 DCM

Sources & evidence

ORD record
ord-312aa5d3fb3344a6910d679d55f38052
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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