Pyridine → HCID 178439652, compound

HRID 1161085Notes

Reaction equation

HRID 1161085 reaction equation
[NH2:1][CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[NH:34][N:33]=[N:32][N:31]=2)[CH:25]=1)[C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=2[CH2:19][CH2:20][CH3:21])=[CH:5][CH:4]=1.[C:35](Cl)(=[O:37])[CH3:36].N1C=CC=CC=1>ClCCl>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]2[CH:22]=[CH:23][C:3]([CH:2]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4[NH:34][N:33]=[N:32][N:31]=4)[CH:25]=3)[NH:1][C:35](=[O:37])[CH3:36])=[CH:4][CH:5]=2)=[C:10]([CH2:19][CH2:20][CH3:21])[C:11]=1[OH:18])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 178439651HCID 178439651, compound

Product 1

HCID 178439652HCID 178439652, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[4-(4-{amino-[3-(1H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone (80 mg, 0.175 mmol), acetyl chloride (15 μL, 0.211 mmol) and dichloromethane (1.5 mL) is stirred at room temperature. Pyridine (50 μL, 0.62 mmol) is added and the mixture is stirred at room temperature 24 hr. An additional portion of acetyl chloride (20 μL, 0.28 mmol) is added and the reaction is stirred an additional 24 hr. The reaction mixture is purified as is via reversed phase C18 preparative chromatography eluting with 4:6 acetonitrile:water (0.1% trifluoroacetic acid) to 8:2 acetonitrile:water (0.1% trifluoroacetic acid) to give the title compound (53 mg, 61%), as a white solid. 1H NMR (DMSO-d6) δ 12.85 (s, 1H), 8.92 (d, 1H), 8.03 (s, 1H), 7.92 (d, 1H), 7.80 (d, 1H), 7.36-7.61 (m, 6H), 6.73 (d, 1H), 6.23 (d, 1H), 5.25 (s, 2H), 2.59-2.62 (m, 5H), 1.97 (s, 3H), 1.46-1.53 (m, 2H), 0.88 (t, 3H). LCMS M−1=498.

Workup

  1. stirringthe mixture is stirred at room temperature 24 hr
  2. stirringthe reaction is stirred an additional 24 hr
  3. customThe reaction mixture is purified
  4. washeluting with 4:6 acetonitrile

Sources & evidence

ORD record
ord-a2079076e22349bc8d9b925aa3f1dfe6
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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