Acryloyl chloride → HCID 136983767, 화합물

HRID 64296노트

반응식

HRID 64296 반응식
[NH2:1][CH2:2][CH:3]1[N:8]2[N:9]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:11]([C:12]([NH2:14])=[O:13])=[C:7]2[NH:6][CH2:5][CH2:4]1.[C:28](Cl)(=[O:31])[CH:29]=[CH2:30]>C(Cl)Cl.CCN(CC)CC>[C:28]([NH:1][CH2:2][CH:3]1[N:8]2[N:9]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:17][CH:16]=3)[C:11]([C:12]([NH2:14])=[O:13])=[C:7]2[NH:6][CH2:5][CH2:4]1)(=[O:31])[CH:29]=[CH2:30]

참가 물질

5

반응물 2

HCID 13140Acryloyl chlorideHCID 1369280997-(Aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

생성물 1

HCID 136983767HCID 136983767, 화합물수율 28%

시약·촉매·용매 2

HCID 8471Triethylamine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 7-(aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide (125 mg, 0.344 mmol) in 5 mL of DCM was added Et3N (four drops) and acryloyl chloride (46.5 mg, 0.52 mmol). After stirring at rt for 30 mins. The mixture was partitioned between water (10 mL) and DCM (5 mL). The organic layer was concentrated and purified by pre-TLC (DCM/MeOH=20/1) to give 40 mg (28%) of product. 1H NMR (400 MHz, DMSO-d6) δ 8.37 (t, J=6.0 Hz, 1H), 7.59 (d, J=8.8 Hz, 2H), 7.54-7.43 (m, 2H), 7.25 (t, J=7.6 Hz, 1H), 7.16-7.11 (m, 4H), 6.76 (s, 1H), 6.33 (dd, J=10.1, 17.0 Hz, 1H), 6.18 (dd, J=1.9, 17.0 Hz, 1H), 5.69 (dd, J=1.9, 10.1 Hz, 1H), 4.28-4.22 (m, 1H), 3.92-3.80 (m, 1H), 3.50-3.30 (m, 3H), 2.14-1.94 (m, 2H). MS (ESI) m/e [M+1]+ 417.9.

후처리

  1. customThe mixture was partitioned between water (10 mL) and DCM (5 mL)
  2. concentrationThe organic layer was concentrated
  3. custompurified by pre-TLC (DCM/MeOH=20/1)

출처 및 근거

ORD 기록
ord-68d81d2671e04ae68e47944ebc088e41
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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