Triethylamine → HCID 46846810, compound

HRID 574628Notes

Reaction equation

HRID 574628 reaction equation
[CH3:1][CH:2]1[NH:6][CH2:5][C:4]2([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[O:3]1.C(N(CC)CC)C.[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl>[F:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:6]2[CH2:5][C:4]3([CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]3)[O:3][CH:2]2[CH3:1])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 197553342,8-Dimethyl-1-oxa-3,8-diazaspiro[4.5]decane

Product 1

HCID 46846810HCID 46846810, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,8-Dimethyl-1-oxa-3,8-diaza-spiro[4.5]decane (1.42 g, 8.38 mmol) was dissolved in dry dichloromethane (5 ml) under argon atmosphere. Distilled triethylamine (1.75 ml, 12.57 mmol) was added and the resulted solution was cooled to 0° C. p-Fluorobenzenesulfonyl chloride (1.63 gr, 8.37 mmol) was added and the reaction flask was allowed to warm to room temperature with stirring, and a white solid started to precipitate. After 30 min of stirring, dichloromethane (90 ml) was added and the resulting solution was washed with water (2×10 ml). The organic phase was dried with anhydrous sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography (silica, CH2Cl2/EtOH/NH4OH 140/10/1) to give AF715 (1.23 g, 98.7% chemical purity) as an off-white powder. 1H NMR (CDCl3, 500 MHz) δ 7.89-7.87 (m, 2H, CHCSO2), 7.27-7.22 (m, 2H, CHCF), 5.05 (q, J=5.23, 1H, CHCH3), 3.33 (d, J=10.26 Hz, 1H, CHHNS), 3.19 (d, J=10.26 Hz, 1H, CHHNS), 2.52-2.42 (m, 1H), 2.34-2.25 (m, 2H), 2.23 (s, 3H, NCH3), 2.18-2.09 (m, 1H), 1.77-1.72 (m, 2H), 1.52 (d, J=5.23 Hz, 3H, CH3CH), 1.25-1.18 (m, 1H), 1.10-1.03 (m, 1H) ppm; 13C NMR (CDCl3, 500 MHz) δ 166.45 and 164.42 (C), 134.0 (C), 130.37 (CH), 130.29 (CH), 116.68 (CH), 116.50 (CH), 86.95 (CH), 66.30 (C), 55.48 (CH2), 52.57 (CH2), 52.11 (CH2), 46.04 (CH3), 35.64 (CH2), 32.84 (CH2), 22.95 (CH3) ppm.

Workup

  1. additionwas added
  2. customto precipitate
  3. stirringAfter 30 min of stirring
  4. additiondichloromethane (90 ml) was added
  5. washthe resulting solution was washed with water (2×10 ml)
  6. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (silica, CH2Cl2/EtOH/NH4OH 140/10/1)
  10. customto give AF715 (1.23 g, 98.7% chemical purity) as an off-white powder

Sources & evidence

ORD record
ord-195bd829b9d444949a6824c58cea892e
Source dataset
uspto-grants-2015_05
Patent number
US09034891B2

Reaction notes

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