Diisopropylethylamine → N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

HRID 1184840Notes

Reaction equation

HRID 1184840 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH2:45][C:46]1[CH:47]=[CH:48][C:49]([CH3:64])=[C:50]([NH:52][C:53]([C:55]2[S:63][C:58]3=[N:59][CH:60]=[CH:61][N:62]=[C:57]3[CH:56]=2)=[O:54])[CH:51]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:45][C:46]1[CH:47]=[CH:48][C:49]([CH3:64])=[C:50]([NH:52][C:53]([C:55]2[S:63][C:58]3=[N:59][CH:60]=[CH:61][N:62]=[C:57]3[CH:56]=2)=[O:54])[CH:51]=1)=[O:7]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2227012-Bromoisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67125547N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride

Product 1

HCID 86680169N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromoisonicotinic acid (160 mg, 0.792 mmol), HATU (331 mg, 0.871 mmol) and DIPEA (0.655 mL, 3.96 mmol) in DMF (8 mL) was stirred at rt for 10 min. N-(5-amino-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide hydrochloride 29 (248 mg, 0.871 mmol) was added and stirred at rt for 3 h. Quenched in 3% citric acid solution and the resulting precipitate was collected. Triturating with acetonitrile gave N-(5-(2-bromoisonicotinamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide (30) (163 mg, 44%). (m/z)=468 and 470 (M+H)+.

Workup

  1. customQuenched in 3% citric acid solution
  2. customthe resulting precipitate was collected
  3. customTriturating with acetonitrile

Sources & evidence

ORD record
ord-a7df7cd3a7374cf785c164a317689ed3
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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