Hydrochloric Acid → HCID 25020401、化合物

HRID 907337ノート

反応式

HRID 907337 の反応式
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:28][CH2:27]3)[CH:18]=[C:17]4[CH:29]=O)[CH:7]=2)[CH2:3][CH2:2]1.[OH:32][CH2:33][C@H:34]1[NH:39][CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([BH3-])#N.[Na+].Cl>ClCCl.C(O)(=O)C.O1CCOCC1.CO>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[C:10]([F:12])[C:9]([CH3:13])=[C:8]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[C:20](=[O:24])[N:19]([CH2:25][CH:26]3[CH2:27][CH2:28]3)[CH:18]=[C:17]4[CH2:29][N:39]3[CH2:38][CH2:37][NH:36][CH2:35][C@H:34]3[CH2:33][OH:32])[CH:7]=2)[CH2:2][CH2:3]1

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 57551841N-Cyclopropyl-3-(2-(cyclopropylmethyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide

生成物 1

HCID 25020401HCID 25020401、化合物

試薬・触媒・溶媒 4

HCID 176Acetic Acid触媒HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

The product of Example 75 step i) (0.4 g), (S)-3-hydroxymethyl-piperazine-1-carboxylic acid, tert-butyl ester (0.83 g) and sodium triacetoxyborohydride (0.81 g) were stirred in dichloromethane (20 mL) at room temperature for 12 hours. A few drops of acetic acid were added and stirring continued for 12 hours. Methanol (10 ml) and sodium cyanoborohydride (0.70 g) were added and stirring continued for a further 12 hours. Methanol (10 ml) and 4M HCl in 1,4-dioxane (10 ml) were added and stirred for 12 hours. The volatiles were removed under vacuum, dilute aqueous ammonia was added and the mixture extracted into dichloromethane. The organics were combined and evaporated under reduced pressure. The residue was purified by HPLC to give the title compound (0.035 g) as a solid.

後処理

  1. stirringstirring
  2. waitcontinued for a further 12 hours
  3. stirringstirred for 12 hours
  4. customThe volatiles were removed under vacuum, dilute aqueous ammonia
  5. additionwas added
  6. extractionthe mixture extracted into dichloromethane
  7. customevaporated under reduced pressure
  8. customThe residue was purified by HPLC

出典と根拠

ORDレコード
ord-e0d336717db14615b82301be90259508
出典データセット
uspto-grants-2011_09
特許番号
US08012979B2

反応ノート

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