1,2-Dichloroethane → HCID 58173379、化合物

HRID 2047195ノート

反応式

HRID 2047195 の反応式
[Br:1][C:2]1[C:3]([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)=[N:4][C:5]2[N:6]([N:9]=[CH:10][C:11]=2[C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:7]=1[NH2:8].C(N(CC)C(C)C)(C)C.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](O)=[O:43].C(Cl)CCl>CN(C=O)C>[NH2:8][C:7]1[N:6]2[N:9]=[CH:10][C:11]([C:12]3[CH:13]=[N:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:5]2[N:4]=[C:3]([C:22]2[CH2:23][CH2:24][N:25]([C:42]([C:38]3[S:37][CH:41]=[CH:40][CH:39]=3)=[O:43])[CH2:26][CH:27]=2)[C:2]=1[Br:1]

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 107002-Thiophenecarboxylic acidHCID 81531DiisopropylethylamineHCID 66733403HCID 66733403、化合物

生成物 1

HCID 58173379HCID 58173379、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6-Bromo-3-(quinolin-3-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-7-amine (0.035 mmol) was charged to a 20 mL scintillation vial. Then DMF (1 ml), N,N-diisopropylethylamine (0.14 mmol, 25 μL), thiophene-2-carboxylic acid (0.039 mmol, 5 mg), and EDC (0.039 mmol, 7.4 mg) were added, respectively. The resulting reaction mixture was stirred at room temperature for 18 hours. Upon completion, the reaction mixture was concentrated in vacuo and purified via reverse-phase preparatory HPLC to yield (4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone (m+H=531.06, retention time=3.74 min). Also recovered was the dehalogenated product, (4-(7-amino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone (m+H=453.24, retention time=3.51 min).

後処理

  1. customThe resulting reaction mixture
  2. concentrationUpon completion, the reaction mixture was concentrated in vacuo
  3. custompurified via reverse-phase preparatory HPLC

出典と根拠

ORDレコード
ord-474d1117e90f4f6b8c638282647c9b04
出典データセット
uspto-grants-2013_11
特許番号
US08591943B2

反応ノート

読み込み中…