Acetic Anhydride → HCID 19771741, compound

HRID 1614592Notes

Reaction equation

HRID 1614592 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([C:10]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[N:35]=[N:36][N:37]([C:39]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[N:38]=3)=[CH:24][CH:23]=2)[C:17]2[CH2:16][NH:15][CH2:14][CH2:13][C:12]=2[N:11]=1)[CH3:9].C(N(CC)CC)C>ClCCl>[C:1]([N:15]1[CH2:14][CH2:13][C:12]2[N:11]=[C:10]([CH2:8][CH3:9])[CH:19]=[C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[N:35]=[N:36][N:37]([C:39]([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)([C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)[C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)[N:38]=4)=[CH:26][CH:27]=3)[C:17]=2[CH2:16]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 19771694HCID 19771694, compound

Product 1

HCID 19771741HCID 19771741, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (78 mg) was added to a stirred solution of 2-ethyl-5,6,7,8-tetrahydro-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl) biphenyl-4-yl)methoxy]-1,6-naphthyridine (500 mg) and triethylamine (150 mg) in dichloromethane (10 ml) under an atmosphere of argon. The solution was left to stand for 20 hours and then volatile material was removed by evaporation. The residue was purified by flash chromatography, eluting with a mixture of methanol/ethyl acetate (1:9 v/v), to give 6-acetyl-2-ethyl-5,6,7,8-tetrahydro-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,6-naphthyridine (350 mg), m.p. 97°-98° C.; NMR (d6 -DMSO, d4 -acetic acid): 1.25(t,3H), 2.15(s,3H), 2.75(q,2H), 2.9-3.0(m,3H), 3.7(m,2H), 4.5(d,2H), 5.2(s,2H), 6.8-7.7 (complex m,23H), 7.75-7.85(m,1H).

Workup

  1. waitThe solution was left
  2. customvolatile material was removed by evaporation
  3. customThe residue was purified by flash chromatography
  4. washeluting with a mixture of methanol/ethyl acetate (1:9 v/v)

Sources & evidence

ORD record
ord-5ced17ee1cac423488e2fda4c07fc938
Source dataset
uspto-grants-1993_03
Patent number
US05198434

Reaction notes

Loading…