Pyridine → HCID 15676075, compound

HRID 2072742Notes

Reaction equation

HRID 2072742 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[F:7][C:8]1[CH:13]=[C:12]([CH:14]([C:16]2[N:17]=[C:18](C)[S:19][CH:20]=2)[CH3:15])[CH:11]=[CH:10][C:9]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:28]([NH:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH3:31].[N:37]1C=CC=C[CH:38]=1>O1CCCC1>[CH2:28]([N:32]([CH2:33][CH2:34][CH2:35][CH3:36])[C:1](=[O:5])[C:2](=[O:3])[N:37]([CH3:38])[C:18]1[S:19][CH:20]=[C:16]([CH:14]([C:12]2[CH:11]=[CH:10][C:9]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[C:8]([F:7])[CH:13]=2)[CH3:15])[N:17]=1)[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8148DibutylamineHCID 65578Oxalyl chlorideHCID 19800953HCID 19800953, compound

Product 1

HCID 15676075HCID 15676075, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To oxalylchloride (1.22 g, 9.61 mmol) in tetrahydrofuran (20 ml) was added dropwise 4-(1-(2-fluoro-4-biphenylyl)ethyl)-2-methylthiazole (1.00 g, 3.20 mmol) in tetrahydrofuran (10 ml). After the addition, the mixture was stirred for 1 h at room temperature, then to the mixture was added dropwise di-n-butylamine (4.14 g, 32.0 mmol) in pyridine (5 ml) under cooling. After the addition, the mixture was stirred for 1 h at room temperature and extracted with ethyl acetate. The extracts were washed with water, dried over and evaporated under reduced pressure to a residue, which was chromatographed to afford N',N'-di-n-butyl-N-methyl-N-(4-(1-(2-fluoro-4-biphenylyl)ethyl)thiazole-2-yl)oxamide (142 mg, 9% yield) as oily substance: NMR(CDCl3) δ 0.89(t, 3H), 0.97(t, 3H), 1.23-1.45(m, 4H), 1.55-1.70 (m, 9H), 3.21(t, 2H), 3.45(t, 3H), 3.63(s, 3H), 4.25(q, 1H), 6.70(s, 1H), 7.08-7.55(m, 8H)ppm; IR(neat) 2950, 1740, 1640, 1480, 1430, 1290, 1100 cm-1.

Workup

  1. additionAfter the addition
  2. temperatureunder cooling
  3. additionAfter the addition
  4. stirringthe mixture was stirred for 1 h at room temperature
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. customdried over and
  8. customevaporated under reduced pressure to a residue, which
  9. customwas chromatographed

Sources & evidence

ORD record
ord-5531bc0ba1ae4b8e8524fe159ec838a2
Source dataset
uspto-grants-1990_04
Patent number
US04914112

Reaction notes

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