Pyrrolidine → HCID 68060919、化合物

HRID 1520049

反応式

HRID 1520049 の反応式
C([BH3-])#N.[Na+].[CH3:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[N:16]=[N:17][N:18]([C:20]2[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=2)[CH:19]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.[BH4-].[Na+]>CC(N(C)C)=O>[CH3:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[C:15]1[N:16]=[N:17][N:18]([C:20]2[CH:27]=[CH:26][C:23]([CH2:24][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:22][CH:21]=2)[CH:19]=1

参加物

6

反応物 4

HCID 31268PyrrolidineHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydrideHCID 715340964-[4-(5-methyl-1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzaldehyde

生成物 1

HCID 68060919HCID 68060919、化合物

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

Sodium cyanoborohydride (166 mg; 2.64 mmol; 4.0 eq.) was added to a solution of 4-[4-(5-methyl-1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzaldehyde (200 mg; 0.66 mmol; 1.0 eq.) and pyrrolidine (1.64 mL; 19.8 mmol; 30 eq.) in DMA (4 mL) and the reaction mixture was stirred at RT. After 12 h, as no product was detected, sodium borohydride was added (100 mg; 2.64 mmol; 4.0 eq.) and the reaction mixture was stirred at RT for 1 hour. Reaction was quenched with water and extracted with EtOAc (twice). Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by preparative HPLC afforded the title compound as a formic acid salt. It was dissolved in MeOH and passed through a SPE-NH2 cartridge. The fractions containing the desired compound were concentrated to dryness affording a yellow gum, which was twice sonicated in 3 mL of Et2O. The suspension obtained was concentrated then dried overnight under high vacuum to afford the title compound as a beige solid. 1H NMR (300 Mz, DMSO-d6) δ: 13.245 (brs, 1H), 9.26 (s, 1H), 8.14-8.13 (m, 1H), 7.99 (d, J=8.5 Hz, 2H), 7.55 (d, J=8.5 Hz, 2H), 7.50 (d, J=8.5 Hz, 1H), 7.27 (dd, J=8.5 Hz, 1.5 Hz, 1H), 3.67 (s, 2H), 2.49-2.45 (m, 7H), 1.74-1.70 (m, 4H). HPLC (Condition A): Rt 2.63 min (purity 99.5%). MS (ESI+): 359.2, MS (ESI−): 357.3.

後処理

  1. stirringthe reaction mixture was stirred at RT for 1 hour
  2. customReaction
  3. customwas quenched with water
  4. extractionextracted with EtOAc (twice)
  5. washCombined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by preparative HPLC

出典と根拠

ORDレコード
ord-78fbfb7406a84d8a9380a508d372e65d
出典データセット
uspto-grants-2015_07
特許番号
US09073892B2

関連ノート

読み込み中…