Triethylamine → HCID 66585128、化合物

HRID 2167412ノート

反応式

HRID 2167412 の反応式
[CH3:1][C@@H:2]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.C(N(CC)CC)C.Cl.[F:24][C:25]1[C:34]2[C:33]([S:35](Cl)(=[O:37])=[O:36])=[CH:32][CH:31]=[CH:30][C:29]=2[CH:28]=[N:27][CH:26]=1>C(#N)C>[F:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][C:33]=2[S:35]([N:8]2[CH2:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:3][C@@H:2]2[CH3:1])(=[O:36])=[O:37])[CH:28]=[N:27][CH:26]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 29981001(S)-tert-Butyl 3-methyl-1,4-diazepane-1-carboxylateHCID 86686407HCID 86686407、化合物

生成物 1

HCID 66585128HCID 66585128、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (S)-tert-butyl 3-methyl-1,4-diazepane-1-carboxylate (2.76 kg, 12.9 mol) and triethylamine (2.97 kg, 29.3 mol) in acetonitrile (45.2 kg) was added 4-fluoroisoquinoline-5-sulfonyl chloride hydrochloride (3.30 kg, 11.7 mol) and washed well with acetonitrile (6.45 kg) while ice cooling under an argon atmosphere. The resulting mixture was stirred for two hours while ice cooling. After confirming the disappearance of the starting materials by high-performance liquid chromatography (HPLC), the reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate (74.3 kg) and a 5% sodium bicarbonate solution (66.0 kg) for extraction. The resulting organic layer was washed with water (66.0 kg) and a 20% aqueous solution of sodium chloride (33.0 kg), and then dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to give the target product as a yellow amorphous product (5.18 kg, quantitative).

後処理

  1. washwashed well with acetonitrile (6.45 kg) while ice cooling under an argon atmosphere
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue were added ethyl acetate (74.3 kg)
  4. extractiona 5% sodium bicarbonate solution (66.0 kg) for extraction
  5. washThe resulting organic layer was washed with water (66.0 kg)
  6. dry with materiala 20% aqueous solution of sodium chloride (33.0 kg), and then dried over anhydrous sodium sulfate
  7. customThe solvent was then evaporated under reduced pressure
  8. customto give the target product as a yellow amorphous product (5.18 kg, quantitative)

出典と根拠

ORDレコード
ord-43241b9850774b84ae57b32b7fc74c62
出典データセット
uspto-grants-2015_06
特許番号
US09045460B2

反応ノート

読み込み中…