Water → HCID 15171354, compound

HRID 654371Notes

Reaction equation

HRID 654371 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][C:7]1[C:8]([CH3:52])=[N:9][C:10]([CH3:51])=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[N:28]=[N:29][N:30]([C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:31]=2)=[CH:17][CH:16]=1.C(N(CC)CC)C.O>ClCCl>[C:1]([NH:5][CH2:6][C:7]1[C:8]([CH3:52])=[N:9][C:10]([CH3:51])=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[N:28]=[N:29][N:30]([C:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:31]=2)=[CH:19][CH:20]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15171343HCID 15171343, compound

Product 1

HCID 15171354HCID 15171354, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(Example 49A): A solution of acetyl chloride (79 mg) in dichloromethane (1 ml) was added to a solution of 3-aminomethyl-2,6-dimethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (628 mg) and triethylamine (101 mg) in dichloromethane (15 ml). The solution was left to stand for 1 hour and then water (15 ml) was added. The organic phase was separated, washed with saturated sodium chloride solution (15 ml) and then dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/dichloromethane (1:19 v/v) to give 3-acetamidomethyl-2,6-dimethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (594 mg), as a foam; NMR (CDCl3): 1.8(s,3H), 2.5(s,3H), 2.6(s,3H), 4.45(d,2H), 5.0(s,2H), 5.6(br t, 1H), 6.6(s,1H), 6.9-7.0(m, 6H), 7.25-7.6 (complex m,16H), 7.95(dd,1H).

Workup

  1. waitThe solution was left
  2. customThe organic phase was separated
  3. washwashed with saturated sodium chloride solution (15 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue was purified by flash chromatography
  7. washeluting with methanol/dichloromethane (1:19 v/v)

Sources & evidence

ORD record
ord-00156a1dfa074b93ac59fc0fd0550178
Source dataset
uspto-grants-1992_07
Patent number
US05130318

Reaction notes

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