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Hydrochloric Acid → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-hydroxymethyl-indol-1-yl)-amide

HRID 2382052
ノート
印刷プレビュー

反応式

HRID 2382052 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH:11][C:12]([C:14]1[C:15]([CH3:26])=[N:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:18][CH:19]=1)=[O:13])[CH:6]=[C:5]2[CH:27]=[O:28].[BH4-].[Na+].Cl>CO.CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH:11][C:12]([C:14]1[C:15]([CH3:26])=[N:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:18][CH:19]=1)=[O:13])[CH:6]=[C:5]2[CH2:27][OH:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 592000434-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-formyl-indol-1-yl)-amide

生成物 1

HCID 591999504-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-hydroxymethyl-indol-1-yl)-amide収率 38.8%

試薬・触媒・溶媒 3

HCID 887Methanol
溶媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-formyl-indol-1-yl)-amide (230 mg, 0.614 mmol) in MeOH (10 mL) is treated with NaBH4 (233 mg, 6.14 mmol) and stirred at rt for 1 h. The mixture is diluted with EtOAc (50 mL) and H2O, neutralized with HCl (conc.), and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by preparative reverse-phase HPLC eluting with 20%-100% MeCN in H2O to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-hydroxymethyl-indol-1-yl)-amide (90 mg, 8%). MS: 378 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 11.92 (s, NH, 1H), 9.27 (s, 1H), 8.81 (d, 1H), 8.47 (d, 1H), 8.05 (m, 1H), 7.61 (m, 1H), 7.44 (m, 3H), 7.10 (m, 1H), 5.00 (t, OH, 1H), 4.66 (d, 2H), 2.78 (s, 3H).

後処理

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialThe combined organic layer is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by preparative reverse-phase HPLC
  6. washeluting with 20%-100% MeCN in H2O

出典と根拠

ORDレコード
ord-687b143eae9d43ce8b4ca6662f73b93d
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08258130B2

反応ノート

読み込み中…

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