Triethylamine → HCID 86690866, compound

HRID 1465563Notes

Reaction equation

HRID 1465563 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:26]=[CH:25][C:9]([O:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([C:18]3[N:19]=[C:20]([NH2:23])[S:21][CH:22]=3)=[C:13]([CH3:24])[CH:12]=2)=[CH:8][CH:7]=1.C([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.[F:34]C1C=C(C=CN=1)C(O)=O.Cl.C(N=C=NCCCN(C)C)C.[OH:56][C:57]1[C:65]2N=NNC=2C=CC=1>C(Cl)Cl>[F:34][C:31]1[CH:30]=[N:29][CH:32]=[CH:33][C:65]=1[C:57]([NH:23][C:20]1[S:21][CH:22]=[C:18]([C:14]2[C:15]([CH3:17])=[CH:16][C:11]([O:10][C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:26][CH:25]=3)=[CH:12][C:13]=2[CH3:24])[N:19]=1)=[O:56]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 3453602-Fluoroisonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86690846HCID 86690846, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86690866HCID 86690866, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-amine (12-6, 180 mg, 0.5 mmol) in CH2Cl2 (2.0 mL) was added triethylamine (0.20 mL, 1.5 mmol) followed by 2-fluoroisonicotinic acid (82.3 mg, 0.70 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (186.3 mg, 1.0 mmol), and hydroxybenzotriazole (131.4 mg, 1.0 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 fluoro-N-(4-{4-(4-(2-methoxyethoxy)phenoxy)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (20, 186.3 mg) as yellow solids in 35% yield: 1H NMR (500 MHz, DMSO-d6) δ 13.10 (s, 1 H), 8.47 (s, 1 H), 7.94-7.95 (m 1H), 7.80 (s, 1 H), 7.19 (s, 1 H), 6.97-7.02 (m, 4 H), 6.69 (s, 2 H), 4.02-4.09 (m, 2 H), 3.65-3.67 (m, 2 H), 3.29 (s, 3 H), 2.05 (m, 6 H). ESI-MS: m/z 494.1 (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-1ae7b7fd91fb4aafba76345d18358cd0
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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