Triethylamine → HCID 178495791, compound

HRID 78436Notes

Reaction equation

HRID 78436 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([CH3:10])=[C:8]([CH3:11])[S:7][C:6]1=[NH:12].CCN(CC)CC.[Br:20][C:21]1[CH:29]=[C:28]([C:30](Cl)=[O:31])[C:24]2[O:25][CH2:26][CH2:27][C:23]=2[CH:22]=1>C1COCC1>[Br:20][C:21]1[CH:29]=[C:28]([C:30](/[N:12]=[C:6]2\[S:7][C:8]([CH3:11])=[C:9]([CH3:10])[N:5]\2[CH2:4][CH2:3][O:2][CH3:1])=[O:31])[C:24]2[O:25][CH2:26][CH2:27][C:23]=2[CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27947985-Bromo-2,3-dihydrobenzo[B]furan-7-carbonyl chlorideHCID 668517233-(2-Methoxy-ethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine

Product 1

HCID 178495791HCID 178495791, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 126A (0.20 g, 1.1 mmol), Et3N (0.45 mL, 3.2 mmol) and 5-bromo-2,3-dihydrobenzo[b]-furan-7-carbonyl chloride (Maybridge, 0.42 g, 1.6 mmol) in 35 mL THF were processed as in Example 126B. The resulting crude material was purified via flash column chromatography (SiO2, 7:3 hexanes:EtOAc) to afford the title compound (0.16 g, 0.39 mmol, 36% yield). 1H NMR (300 MHz, CDCl3) δ ppm 2.24 (s, 3H), 2.28 (s, 3H), 3.23 (t, J=8.5 Hz, 2H), 3.33 (s, 3H), 3.78-3.87 (m, 2H), 4.45-4.56 (m, 2H), 4.70-4.81 (m, 2H), 7.35-7.39 (m, 1H), 8.09 (d, J=2.0 Hz, 1H); MS (DCI/NH3) m/z 411, 413 (M+H)+; Anal. calculated for C17H19BrN2O3S.0.3H2O: C, 49.00; H, 4.74; N, 6.72. Found: C, 48.91; H, 4.36; N, 6.57.

Workup

  1. customThe resulting crude material was purified via flash column chromatography (SiO2, 7:3 hexanes:EtOAc)

Sources & evidence

ORD record
ord-a23c1f436b544ad3a71b244bac6ff9c5
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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