Triethylamine → HCID 19099543, compound

HRID 1974935Notes

Reaction equation

HRID 1974935 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32]([C:33]([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)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:53][OH:54])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH3:62][S:63](Cl)(=[O:65])=[O:64]>O1CCCC1>[CH2:1]([C:5]1[N: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:32]([C:33]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[N:31]=[N:30][N:29]=3)=[CH:20][CH:21]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:53][O:54][S:63]([CH3:62])(=[O:65])=[O:64])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19099540HCID 19099540, compound

Product 1

HCID 19099543HCID 19099543, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 0.250 g of 2-butyl-6-(hydroxymethyl)-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-4(3H)-quinazolinone and 0.246 ml of triethylamine in 5.0 ml of tetrahydrofuran is cooled to -78° C. and 0.137 ml of methanesulfonyl chloride added. The reaction mixture is allowed to warm to room temperature and continue stirring for 18 hours. The reaction mixture is partitioned between chloroform and water. The organic layer is washed with aqueous 5% HCl, water and saturated aqueous sodium bicarbonate then dried with magnesium suflate and evaporated to afford 0.278 g of the desired product. FAB MASS SPEC 787 (M+H).

Workup

  1. customThe reaction mixture is partitioned between chloroform and water
  2. washThe organic layer is washed with aqueous 5% HCl, water and saturated aqueous sodium bicarbonate
  3. dry with materialthen dried with magnesium suflate
  4. customevaporated

Sources & evidence

ORD record
ord-4e0b0f491bb642619c24833515107ea3
Source dataset
uspto-grants-1994_02
Patent number
US05284852

Reaction notes

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