Diisopropylethylamine → 2-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide

HRID 1184831Notes

Reaction equation

HRID 1184831 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([OH:13])=O)[S:10][C:5]2=[N:4][CH:3]=1.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.[NH2:48][C:49]1[CH:50]=[C:51]([NH:56][C:57](=[O:69])[C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([C:67]#[N:68])([CH3:66])[CH3:65])[CH:59]=2)[CH:52]=[CH:53][C:54]=1[CH3:55]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([NH:48][C:49]3[CH:50]=[C:51]([NH:56][C:57](=[O:69])[C:58]4[CH:63]=[CH:62][CH:61]=[C:60]([C:64]([C:67]#[N:68])([CH3:65])[CH3:66])[CH:59]=4)[CH:52]=[CH:53][C:54]=3[CH3:55])=[O:13])[S:10][C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67125541N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochlorideHCID 866801662-Chlorothieno[2,3-b]pyrazine-6-carboxylic acid

Product 1

HCID 547564232-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamideYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chlorothieno[3,2-b]pyrazine-6-carboxylic acid 23 (350 mg, 1.631 mmol), HATU (744 mg, 1.957 mmol) and DIPEA (0.809 mL, 4.89 mmol) in DMF (8 mL) was stirred for 15 min. N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochloride 6 (538 mg, 1.631 mmol) was added and stirred overnight at rt. Quenched in citric acid solution (3%) and the resulting precipitate was collected. Triturating in acetonitrile gave the title compound 2-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 24 (450 mg, 56%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.26 (s, 3H), 7.32 (d, J=8.2 Hz, 1H), 7.58-7.68 (m, 2H), 7.76 (d, J=7.8 Hz, 1H), 7.87 (d, J=1.9, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.05 (s, 1H), 8.49 (s, 1H), 8.89 (s, 1H), 10.38 (s, 1H), 10.59 (s, 1H). (m/z)=490 and 492 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-85892e038ccc49ae97a87428ffd8c07d
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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