Hydroxyamine hydrochloride → 3,4-dihydro-2-quinolone (DHQ) derivative, 21

HRID 1247509노트

반응식

HRID 1247509 반응식
Cl.[NH2:2][OH:3].C[O-].[Na+].[Cl:7][C:8]1[S:32][C:11]2[NH:12][C:13]([C:15]([NH:17][CH:18]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:28][C:29]#[N:30])[C:19]3=[O:31])=[O:16])=[CH:14][C:10]=2[CH:9]=1>CO.C1COCC1.CCOC(C)=O>[NH2:30]/[C:29](=[N:2]\[OH:3])/[CH2:28][N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH:18]([NH:17][C:15]([C:13]2[NH:12][C:11]3[S:32][C:8]([Cl:7])=[CH:9][C:10]=3[CH:14]=2)=[O:16])[C:19]1=[O:31]

참가 물질

7

반응물 3

HCID 443297Hydroxyamine hydrochlorideHCID 104526402-Chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideHCID 10942334Sodium Methoxide

생성물 1

HCID 100249933,4-dihydro-2-quinolone (DHQ) derivative, 21수율 101.2%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Hydroxylamine hydrochloride (181 mg, 2.60 mmol) in MeOH (5 mL) was added to a solution of NaOMe in MeOH (10.20 mL, 0.25M) under an inert atmosphere followed by 2-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 27; 500 mg, 1.30 mmol) in THF (7 mL) then stirred for 18 hours. The mixture was diluted with EtOAc (100 mL) and washed with brine (25 mL), dried (Na2SO4), filtered and evaporated to afford the title product (550 mg, 100%) as a pale brown solid.

후처리

  1. washwashed with brine (25 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-29a74013d9db420f87d9481a6a54a992
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129249B2

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