Diisopropylethylamine → N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-oxo-1,2-dihydrothieno[2,3-b]pyrazine-6-carboxamide

HRID 1184893Notes

Reaction equation

HRID 1184893 reaction equation
[O:1]=[C:2]1[NH: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=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH2:46][C:47]1[CH:48]=[C:49]([NH:54][C:55](=[O:67])[C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([C:65]#[N:66])([CH3:64])[CH3:63])[CH:57]=2)[CH:50]=[CH:51][C:52]=1[CH3:53]>CN(C=O)C>[C:65]([C:62]([C:58]1[CH:57]=[C:56]([CH:61]=[CH:60][CH:59]=1)[C:55]([NH:54][C:49]1[CH:50]=[CH:51][C:52]([CH3:53])=[C:47]([NH:46][C:11]([C:9]2[S:10][C:5]3[N:4]=[CH:3][C:2](=[O:1])[NH:7][C:6]=3[CH:8]=2)=[O:13])[CH:48]=1)=[O:67])([CH3:64])[CH3:63])#[N:66]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67125541N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochlorideHCID 671255862-Oxo-1,2-dihydrothieno[3,2-b]pyrazine-6-carboxylic acid

Product 1

HCID 67125574N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-oxo-1,2-dihydrothieno[2,3-b]pyrazine-6-carboxamideYield 0.308%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 2-oxo-1,2-dihydrothieno[3,2-b]pyrazine-6-carboxylic acid 84 (27 mg, 0.138 mmol), TBTU (48.6 mg, 0.151 mmol) and DIPEA (0.068 mL, 0.413 mmol) in DMF (1 mL) was stirred for 15 min. N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochloride 6 (45.4 mg, 0.138 mmol) in DMF (1 mL) was added and stirred overnight at 50° C. Quenched with water and extracted with EtOAc. Organic layer was washed with water, dried and evaporated. Purification by HPLC gave the title compound N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-2-oxo-1,2-dihydrothieno[2,3-b]pyrazine-6-carboxamide 85 (0.2 mg, 0.308%). (m/z)=472 (M+H)+.

Workup

  1. customQuenched with water
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with water
  4. customdried
  5. customevaporated
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-8b9f78e6ec0244f595b40f71b83e548d
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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