Hydrochloric Acid → HCID 25020401, 화합물

HRID 907337노트

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HRID 907337 반응식
[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

참가 물질

10

반응물 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

생성물 1

HCID 25020401HCID 25020401, 화합물

시약·촉매·용매 4

HCID 176Acetic Acid촉매HCID 887Methanol용매2회HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e0d336717db14615b82301be90259508
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012979B2

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