Acryloyl chloride → HCID 136983767、化合物

HRID 64296ノート

反応式

HRID 64296 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 136983767HCID 136983767、化合物収率 28%

試薬・触媒・溶媒 2

HCID 8471Triethylamine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-68d81d2671e04ae68e47944ebc088e41
出典データセット
uspto-grants-2016_09
特許番号
US09447106B2

反応ノート

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