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Sodium borohydride → 3-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamido)-3-(hydroxymethyl)pyridin-2-yl)benzoic acid

HRID 2188968
ノート
印刷プレビュー

反応式

HRID 2188968 の反応式
[BH4-].[Na+].[F:3][C:4]1([F:38])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]([NH:18][C:19]4[N:24]=[C:23]([C:25]5[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=5)[C:28]([OH:30])=[O:29])[C:22]([C:34](OC)=[O:35])=[CH:21][CH:20]=4)=[O:17])[CH2:15][CH2:14]3)=[CH:12][C:6]=2[O:5]1>C1COCC1>[F:38][C:4]1([F:3])[O:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]3([C:16]([NH:18][C:19]4[N:24]=[C:23]([C:25]5[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=5)[C:28]([OH:30])=[O:29])[C:22]([CH2:34][OH:35])=[CH:21][CH:20]=4)=[O:17])[CH2:14][CH2:15]3)=[CH:12][C:6]=2[O:5]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 4311764Sodium borohydride2 回HCID 591659443-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-(methoxycarbonyl)pyridin-2-yl)benzoic acid

生成物 1

HCID 591661043-(6-(1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-carboxamido)-3-(hydroxymethyl)pyridin-2-yl)benzoic acid収率 40%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

NaBH4 (53 mg, 1.4 mmol) was added to a solution of 3-(6-(1-(2,2-difluorobenzo-[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-(methoxycarbonyl)pyridin-2-yl)benzoic acid (140 mg, 0.28 mmol) in THF (3 mL). The reaction was stirred at 50° C. for 5 hours. Additional NaBH4 (53 mg, 1.4 mmol) was added and the reaction was stirred at 50° C. overnight. The reaction was quenched by the addition of water and the reaction mixture was partitioned between CH2Cl2 and 1N HCl. The organic layer was dried (MgSO4) and concentrated. CH2Cl2 was added to the residue and a precipitate formed which was filtered to obtain the product as a white solid (52 mg, 40%). ESI-MS m/z calc. 468.1. found 469.5 (M+1)+. Retention time 1.64 minutes. 1H NMR (400 MHz, DMSO-d6) δ 9.10 (s, 1H), 8.06 (d, J=1.5 Hz, 1H), 8.01-7.93 (m, 3H), 7.76 (d, J=7.5 Hz, 1H), 7.57-7.54 (m, 2H), 7.40-7.34 (m, 2H), 5.33 (s, 1H), 4.38 (s, 2H), 1.53-1.51 (m, 2H), 1.19-1.16 (m, 2H).

後処理

  1. stirringthe reaction was stirred at 50° C. overnight
  2. customThe reaction was quenched by the addition of water
  3. customthe reaction mixture was partitioned between CH2Cl2 and 1N HCl
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. additionCH2Cl2 was added to the residue
  7. customa precipitate formed which
  8. filtrationwas filtered

出典と根拠

ORDレコード
ord-a590a227fdc040fdbbf1fbbaa022fad0
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324207B2

反応ノート

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