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

HRID 1247509ノート

反応式

HRID 1247509 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-29a74013d9db420f87d9481a6a54a992
出典データセット
uspto-grants-2006_10
特許番号
US07129249B2

反応ノート

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