Dimethylformamide → HCID 178426563, compound

HRID 1184889Notes

Reaction equation

HRID 1184889 reaction equation
N[C:2]1[C:10]2[C:5](=NC=CN=2)S[C:3]=1[C:11]([OH:13])=O.CN(C(ON1N=N[C:24]2[CH:25]=[CH:26][CH:27]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:38]CN(C(C)C)C(C)C.[NH2:47][C:48]1[CH:49]=[CH:50][C:51]([CH3:67])=[C:52]([NH:54][CH:55]([C:58]2[S:66][C:61]3=[N:62][CH:63]=[CH:64][N:65]=[C:60]3[CH:59]=2)[C:56]#[N:57])[CH:53]=1.C[N:69]([CH:71]=O)C>>[C:71]([C:25]([C:26]1[CH:27]=[C:3]([CH:2]=[CH:10][CH:5]=1)[C:11]([NH:47][C:48]1[CH:49]=[CH:50][C:51]([CH3:67])=[C:52](/[N:54]=[C:55](\[C:56]#[N:57])/[C:58]2[S:66][C:61]3=[N:62][CH:63]=[CH:64][N:65]=[C:60]3[CH:59]=2)[CH:53]=1)=[O:13])([CH3:38])[CH3:24])#[N:69]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 122257127-Aminothieno[2,3-b]pyrazine-6-carboxylic acidHCID 671255562-(5-Amino-2-methylphenylamino)-2-(thieno[2,3-b]pyrazin-6-yl)acetonitrile

Product 1

HCID 178426563HCID 178426563, compoundYield 5.3%

Procedure

A solution of 7-aminothieno[2,3-b]pyrazine-6-carboxylic acid 8 (33.8 mg, 0.179 mmol), HATU (74.1 mg, 0.195 mmol), DIPEA (0.081 mL, 0.488 mmol) in DMF (1 mL) was stirred at rt for 30 min. 2-(5-amino-2-methylphenylamino)-2-(thieno[2,3-b]pyrazin-6-yl)acetonitrile 78 (48 mg, 0.163 mmol) was added and stirred overnight at rt. Quenched with citric acid solution (3%) and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated. Purification by HPLC gave the title compound (E)-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carbimidoyl cyanide 79 (4 mg, 5.30%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.26 (s, 3H), 7.41 (d, J=8.2 Hz, 1H), 7.63 (m, 2H), 7.77 (m, 1H), 7.86 (d, J=2.0 Hz, 1H), 7.97 (d, J=7.4 Hz, 1H), 8.06 (s, 1H), 8.36 (s, 1H), 8.80 (d, J=2.3 Hz, 1H), 8.93 (d, J=2.3 Hz, 1H), 10.49 (s, 1H). (m/z)=465 (M+H)+.

Workup

  1. customQuenched with citric acid solution (3%)
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with brine
  4. customdried
  5. customevaporated
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-ee59c2a79bed4505806179ed5440cec6
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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