Benzoyl chloride → HCID 18782681, compound

HRID 1420697Notes

Reaction equation

HRID 1420697 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23]([C:24]([F:27])([F:26])[F:25])=[N:22][N:21]=[N:20]2)=[CH:15][C:14]=1[C:28]1[CH2:29][O:30][C:31]2([CH2:37][CH2:36][CH2:35][NH:34][CH2:33]2)[CH:32]=1>N1C=CC=CC=1>[C:1]([N:34]1[CH2:35][CH2:36][CH2:37][C:31]2([O:30][CH2:29][C:28]([C:14]3[CH:15]=[C:16]([N:19]4[C:23]([C:24]([F:25])([F:26])[F:27])=[N:22][N:21]=[N:20]4)[CH:17]=[CH:18][C:13]=3[O:12][CH3:11])=[CH:32]2)[CH2:33]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 18782720HCID 18782720, compound

Product 1

HCID 18782681HCID 18782681, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Benzoyl chloride (0.10 ml, 0.86 mmol) was added to a solution of 3-(2-methoxy-5-(5-trifluoromethyl-1H-tetrazol-1-yl)phenyl)-1-oxa-7-azaspiro[4,5]dec-3-ene hydrochloride (Desc. 11; 0.33 g, 0.79 mmol) in pyridine (5 ml) at 0° C. The mixture was stirred at 0° C. for 11/2 hours, allowed to warm to room temperature and concentrated in vacuo. 1M Hydrochloric acid (50 ml) was added to the residue and the mixture extracted with dichloromethane (2×25 ml). The combined extracts were dried (MgSO4), concentrated and the residue purified by flash chromatography, eluting with 21/2% methanol in dichloromethane, to afford the title compound as a white foam (0.26 g, 68%), which was recrystallised from ethyl acetate/hexane, m.p. 154°-156° C.; (Found: C, 59.29; H, 4.45; N, 14.15, C24H33F3N5O3 requires C, 59.38; H, 4.57; N, 14.43%); δH (360MHz, DMSO-d6, 353K) 1.62 (1H, m), 1.75-1.85 (3H, m), 3.19 (1H, m), 3.39 (1H, br d, J 12Hz), 3.49 (1H, m), 3.80 (1H, m), 3.94 (3H, s, ArOCH3), 4.74 (1H, m, 2-CHaHB), 4.89 (1H, dd, J 12.6, 1.9Hz, 2--CHAHB), 6.52 (1H, br s, 4--CH=), 7.30 (1H, d, J 8.8Hz, 3'-H), 7.37 (5H, m, PhH), 7.55 (1H, d, J 2.6Hz, 6'-H), 7.63 (1H, dd, J 8.8, 2.6Hz, 4'-H); m/z (ES+) 486 ([M+H]+).

Workup

  1. temperatureto warm to room temperature
  2. concentrationconcentrated in vacuo
  3. addition1M Hydrochloric acid (50 ml) was added to the residue
  4. extractionthe mixture extracted with dichloromethane (2×25 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue purified by flash chromatography
  8. washeluting with 21/2% methanol in dichloromethane

Sources & evidence

ORD record
ord-8638ba09459343839d95d3dff2b5e3f8
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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