1,2-Dichloroethane → HCID 58173379, 화합물

HRID 2047195노트

반응식

HRID 2047195 반응식
[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]

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 107002-Thiophenecarboxylic acidHCID 81531DiisopropylethylamineHCID 66733403HCID 66733403, 화합물

생성물 1

HCID 58173379HCID 58173379, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-474d1117e90f4f6b8c638282647c9b04
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591943B2

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