Triethylamine → HCID 14950485, compound

HRID 1769073Notes

Reaction equation

HRID 1769073 reaction equation
C(N(CC)CC)C.CS([Cl:12])(=O)=O.O[CH2:14][C:15]1[C:16]([CH3:60])=[N:17][C:18]([CH3:59])=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:36]=[N:37][N:38]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:39]=2)=[CH:25][CH:24]=1>ClCCl.O>[Cl:12][CH2:14][C:15]1[C:16]([CH3:60])=[N:17][C:18]([CH3:59])=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[N:36]=[N:37][N:38]([C:40]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[N:39]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14950483HCID 14950483, compound

Product 1

HCID 14950485HCID 14950485, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.2 ml) and methanesulphonyl chloride (1.24 ml) were added to a solution of compound B (10.0 g) in dichloromethane (150 ml). The solution was left to stand for 20 hours and then diluted with water (150 ml). The organic phase was separated, washed with saturated sodium chloride solution (150 ml), and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with a mixture of methanol and dichlormethane (1:19 v/v) to give 3-chloromethyl-2,6-dimethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (C) (8.5 g), as a white solid, m.p. 110°-112° C.; NMR (d6 -DMSO/d4 -acetic acid): 2.5(s,3H), 2.65(s,3H), 4.75(s,2H), 5.45(s,2H), 6.9-7.9 (complex m,24H).

Workup

  1. waitThe solution was left
  2. customThe organic phase was separated
  3. washwashed with saturated sodium chloride solution (150 ml)
  4. dry with materialdried (MgSO4)
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by flash chromatography
  7. washeluting with a mixture of methanol and dichlormethane (1:19 v/v)

Sources & evidence

ORD record
ord-988707c374bb43db9be2cbadc0105971
Source dataset
uspto-grants-1995_01
Patent number
US05380730

Reaction notes

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