Triethylamine → HCID 71586184, compound

HRID 1465542Notes

Reaction equation

HRID 1465542 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[C:4]([CH3:15])[C:3]=1[C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1.C(N(CC)CC)C.Cl.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:15][C:4]1[CH:5]=[C:6]([S:8][C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)[CH:7]=[C:2]([CH3:1])[C:3]=1[C:16]1[N:17]=[C:18]([NH:21][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[S:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 86690843HCID 86690843, compound

Product 1

HCID 71586184HCID 71586184, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2,6-dimethyl-4-(pyrazin-2-ylthio)phenyl)thiazol-2-amine (11-5, 500 mg, 1.6 mmol) in CH2Cl2 (10.0 ml) was added triethylamine (0.7 ml, 4.0 mmol) followed by isonicotinoyl chloride hydrochloride (707.7 mg, 4.8 mmol). The reaction mixture was stirred at room temperature overnight. The solution was concentrated under reduced pressure and added with hot water. The resultant precipitate was filtered and dried under vacuum to give N-{4-(2,6-dimethyl-4-(pyrazin-2-ylthio)phenyl)thiazol-2-yl}isonicotinamide (11, 392.5 mg) as white solids in 59% yield: 1H NMR (500 MHz, DMSO-d) δ 13.1 (s, 1 H), 8.81 (d, J=5.7 Hz, 2 H), 8.50 (s, 1 H), 8.41 (s, 1 H), 8.36 (s, 1H), 8.00 (d, J=5.7 Hz, 2 H), 7.41 (s, 2 H), 7.30 (s, 1 H), 2.13 (s, 6 H). ESI-MS: m/z 420.2 (M+H)+.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionadded with hot water
  3. filtrationThe resultant precipitate was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-79e26041c7c04bb6b7ea7edcd1a52d61
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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