Triethylamine → HCID 178441651, compound

HRID 1655569Notes

Reaction equation

HRID 1655569 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)=[N:5][C:6]([CH2:9][CH2:10][CH2:11][CH3:12])=[N:7][CH:8]=1.C(N(CC)CC)C.[CH3:58][S:59](Cl)(=[O:61])=[O:60]>C1COCC1>[CH2:9]([C:6]1[N:5]=[C:4]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:3]([CH2:2][NH:1][S:59]([CH3:58])(=[O:61])=[O:60])=[CH:8][N:7]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19791864HCID 19791864, compound2×

Product 1

HCID 178441651HCID 178441651, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Aminomethyl-2-butyl-4-{N-[(2'-[N-triphenylmethyl-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine, the intermediate from Example 32, is dissolved in THF containing triethylamine and treated with one equivalent of methanesulfonyl chloride. After the reaction is complete according to TLC analysis, the reaction mixture is washed with dilute aqueous sodium bicarbonate solution, dried and concentrated in vacuo to give 2-butyl-5-[methanesulfonamidomethyl]-4-{N-[N-triphenylmethyl-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine. The triphenylmethyl group is removed, as described in Example 1D, to give the title compound.

Workup

  1. washthe reaction mixture is washed with dilute aqueous sodium bicarbonate solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto give 2-butyl-5-[methanesulfonamidomethyl]-4-{N-[N-triphenylmethyl-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine
  5. customThe triphenylmethyl group is removed

Sources & evidence

ORD record
ord-621773ae0660411188f38d6683831c55
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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