Sodium t-butoxide → 5-(5-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

HRID 1921749Notes

Reaction equation

HRID 1921749 reaction equation
OC1C=CC(C[NH:7]C(=O)C2C=CC(NC3C4N(C=CN=4)C(C4C=NNC=4)=CN=3)=CC=2)=CC=1.[Br:33][C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37](Br)=[N:36][CH:35]=1.[CH2:44]([N:46]([CH2:59][CH3:60])[CH2:47][CH2:48][NH:49][C:50]([C:52]1[CH:57]=[CH:56][C:55]([NH2:58])=[CH:54][N:53]=1)=[O:51])[CH3:45].CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C1(C)C=CC=CC=1>[NH3:7].[CH2:59]([N:46]([CH2:44][CH3:45])[CH2:47][CH2:48][NH:49][C:50]([C:52]1[CH:57]=[CH:56][C:55]([NH:58][C:37]2[C:38]3[N:39]([CH:40]=[CH:41][N:42]=3)[C:34]([Br:33])=[CH:35][N:36]=2)=[CH:54][N:53]=1)=[O:51])[CH3:60]

Participants

9

Reactant 4

HCID 23676156Sodium t-butoxideHCID 24857547N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamideHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazineHCID 590231165-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

Product 2

HCID 222AmmoniaHCID 590231155-(5-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amideYield 72%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (0.272 g, 0.982 mmol), 5-amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide (0.197 g, 0.835 mmol), NaOtBu (0.132 g, 1.37 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), Xantphos (22 mg, 0.038 mmol) and toluene (3 mL). The crude material is purified by silica gel column chromatography eluting with DCM followed by 94:6 DCM:NH3 (7M in MeOH) to afford the title compound (0.263 g, 72%). HPLC (254 nm) Rt 2.09 min (72%).

Workup

  1. customThe crude material is purified by silica gel column chromatography
  2. washeluting with DCM

Sources & evidence

ORD record
ord-0e28abf482c54765b60bb55c66858fdd
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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