Trifluoroacetic acid → [3-Butyl-6,7-dihydro-5-[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]imidazo[1,5-a]pyridin-8(5H)-ylidene]acetic acid

HRID 22046ノート

反応式

HRID 22046 の反応式
[CH2:1]([C:5]1[N:9]2[CH:10]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[NH:38][N:37]=[N:36][N:35]=4)=[CH:24][CH:23]=3)[CH2:11][CH2:12][C:13](=[CH:14][C:15]([O:17]C(C)(C)C)=[O:16])[C:8]2=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O>>[CH2:1]([C:5]1[N:9]2[CH:10]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]4[NH:38][N:37]=[N:36][N:35]=4)=[CH:24][CH:23]=3)[CH2:11][CH2:12][C:13](=[CH:14][C:15]([OH:17])=[O:16])[C:8]2=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 178441592HCID 178441592、化合物

生成物 1

HCID 178441590[3-Butyl-6,7-dihydro-5-[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]imidazo[1,5-a]pyridin-8(5H)-ylidene]acetic acid収率 96%

実験手順

To a solution of 32 mg (0.0627 mmol) of tert-butyl ester (the title compound of Example 15) in 2 mL of CDCl3 at room temperature was added 0.5 mL of TFA, and the progress of the reaction was monitored by 1H NMR. The resulting yellow solution was stirred at room temperature for 1 h and concentrated in vacuo. The crude product was dissolved in a minimum amount of methanol, diluted with methylene chloride, then triturated with ether and hexane at 5° C. to give 27 mg (96%) of the title compound of Example 16 as a solid: mp 154.0°-155.5° C. (decomposed); 1H NMR (CD3OD) δ 0.84 (t, J=7.5 Hz, 3H), 1.2-1.45 (m, 2H), 1.45-1.63 (m, 2H), 2.25-2.55 (m, 3H), 2.60-2.9 (m, 2H), 3.52-3.7 (m, 1H), 5.95 (br s, 1 H), 6.59 (s, 1H), 6.99 (d, J=7.5 Hz, 2H), 7.19 (d, J=7.7 Hz, 2H), 7.50-7.62 (m, 2H, 7.67 (d, J=7.2 Hz, 2H), 8.16 (s, 1H); HRMS. calcd for M+H: 455.2195. Found: 455.2195.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude product was dissolved in a minimum amount of methanol
  3. additiondiluted with methylene chloride
  4. customtriturated with ether and hexane at 5° C.

出典と根拠

ORDレコード
ord-42901f26d2324dcd8f258d6688626506
出典データセット
uspto-grants-1995_06
特許番号
US05426105

反応ノート

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