Water → 3-(2-cyanopropan-2-yl)-N-(4-methyl-3-(thieno[2,3-b]pyrazin-6-ylmethylamino)phenyl)benzamide

HRID 1184861Notes

Reaction equation

HRID 1184861 reaction equation
Br[CH2:2][C:3]1[S:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[CH:4]=1.Cl.[NH2:13][C:14]1[CH:15]=[C:16]([NH:21][C:22](=[O:34])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([C:32]#[N:33])([CH3:31])[CH3:30])[CH:24]=2)[CH:17]=[CH:18][C:19]=1[CH3:20].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:32]([C:29]([C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[C:22]([NH:21][C:16]1[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([NH:13][CH2:2][C:3]2[S:11][C:10]3=[N:9][CH:8]=[CH:7][N:6]=[C:5]3[CH:4]=2)[CH:15]=1)=[O:34])([CH3:30])[CH3:31])#[N:33]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67125541N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochlorideHCID 671255506-(Bromomethyl)thieno[3,2-b]pyrazine

Product 1

HCID 671256603-(2-cyanopropan-2-yl)-N-(4-methyl-3-(thieno[2,3-b]pyrazin-6-ylmethylamino)phenyl)benzamideYield 6.23%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-(bromomethyl)thieno[3,2-b]pyrazine 47 (50 mg, 0.218 mmol), N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide hydrochloride 6 (72 mg, 0.218 mmol) and potassium carbonate (90 mg, 0.655 mmol) in acetonitrile (2 mL) was stirred overnight at 50° C. Water was added and extracted with EtOAc. Organic layer was washed with brine, dried and evaporated. Purification by HPLC gave the title compound 3-(2-cyanopropan-2-yl)-N-(4-methyl-3-(thieno[2,3-b]pyrazin-6-ylmethylamino)phenyl)benzamide 48 (6 mg, 6.23%). NMR (400 MHz, DMSO-d6) 1.71 (s, 6H), 2.16 (s, 3H), 4.72 (d, J=5.5 Hz, 2H), 6.02 (t, J=6.2 Hz, 1H), 6.98 (s, 2H), 7.08 (s, 1H), 7.54 (m, 2H), 7.70 (d, J=7.8 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.92 (t, J=1.6 Hz, 1H), 8.50 (d, J=2.3 Hz, 1H), 8.66 (d, J=2.3 Hz, 1H), 10.00 (s, 1H). (m/z)=442 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-cc8499cf39b9454c9b6ca4bdc40c35ea
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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