Acetyl chloride → HCID 10236818, compound

HRID 2306871Notes

Reaction equation

HRID 2306871 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].CCN(C(C)C)C(C)C.[Cl:18][C:19]1[C:27]([CH2:28]Cl)=[CH:26][C:22]2[O:23][CH2:24][O:25][C:21]=2[CH:20]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].C(O)C(N)(CO)CO>ClCCl.CN(C1C=CN=CC=1)C>[Cl:18][C:19]1[C:27]([CH2:28][S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:37](=[O:39])[CH3:38])=[CH:26][C:22]2[O:23][CH2:24][O:25][C:21]=2[CH:20]=1

Participants

9

Reactant 6

HCID 6367Acetyl chlorideHCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 87132-AminothiophenolHCID 81531DiisopropylethylamineHCID 901136-Chloropiperonyl chloride

Product 1

HCID 10236818HCID 10236818, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-aminothiophenol (0.4 mmol) and PS-DIEA resin (0.35 g, 3.76 mmol/g) were combined in dichloromethane (4 mL) and agitated for 10 min. 5-chloro-6-(chloromethyl)-1,3-benzodioxole (0.3 mmol) was added and the reaction agitated for a further 3 h. Reaction was treated with MP BH4− resin (Argonaut 3.16 mmol/g) for 2 h then filtered. The filtrate was combined with triethylamine (0.4 mmol), PS-DMAP resin (0.1 g) and acetyl chloride (0.4 mmol). Agitate for 18 h then treat the reaction with PS-trisamine resin for 4 h, filter and remove the solvent under a stream of nitrogen. The residue was purified by reverse phase chromatography. 1H NMR (CDCl3) δ 8.38-8.32 (m, 2 H), 7.52 (m, 1 H), 7.38-7.32 (m, 1 H), 7.07-7.02 (m, 1 H), 6.83 (s, 1 H), 6.25 (s, 1 H), 5.93 (s, 2 H), 3.90 (s, 2 H), 2.09 (s, 3 H);MS (ESI+) for C16H14ClNO3S m/z 336 (M+H)+.

Workup

  1. stirringthe reaction agitated for a further 3 h
  2. customReaction
  3. additionwas treated with MP BH4− resin (Argonaut 3.16 mmol/g) for 2 h
  4. filtrationthen filtered
  5. stirringAgitate for 18 h
  6. additionthen treat
  7. filtrationfilter
  8. customremove the solvent under a stream of nitrogen
  9. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-298166010f6042ec8346de0cf95438a8
Source dataset
uspto-grants-2004_12
Patent number
US06828446B2

Reaction notes

Loading…