Ethyl isocyanate → HCID 15171356, compound

HRID 1614776Notes

Reaction equation

HRID 1614776 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][CH2:7][C:8]1[C:9]([CH3:53])=[N:10][C:11]([CH3:52])=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[N:29]=[N:30][N:31]([C:33]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:32]=2)=[CH:18][CH:17]=1>ClCCl>[CH3:53][C:9]1[C:8]([CH2:7][NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[C:13]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31]([C:33]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:32]=3)=[CH:20][CH:21]=2)[CH:12]=[C:11]([CH3:52])[N:10]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 15171343HCID 15171343, compound

Product 1

HCID 15171356HCID 15171356, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Example 51A): A solution of ethyl isocyanate (71 mg) and 3-aminomethyl-2,6-dimethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl) biphenyl-4-yl)methoxy]pyridine (628 mg) in dichloromethane (15 ml) was left to stand for 2 hours. The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/dichloromethane (7:93 v/v), to give 2,6-dimethyl-3-(ethylaminocarbonylamino)methyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (602 mg), as a foam: NMR (CDCl3): 1.0(t,3H), 2.5(s,3H), 2.65(s,3H), 3.0-3.1(m,2H), 4.1(br t, 1H), 4.4(d,2H), 4.5(br d, 1H), 5.0(s,2H), 6.6(s,2H), 6.8-7.0(m,6H), 7.1-7.55 (complex m,16H), 7.9(dd,1H).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was purified by flash chromatography
  3. washeluting with methanol/dichloromethane (7:93 v/v)

Sources & evidence

ORD record
ord-19bdab9d377742c1a31f8c240cfa8729
Source dataset
uspto-grants-1993_03
Patent number
US05198439

Reaction notes

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