Dimethyl Sulfoxide → 7-(Aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 64295ノート

反応式

HRID 64295 の反応式
[NH2:1][CH2:2][CH:3]1[N:8]2[N:9]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)[C:11]([C:12]#[N:13])=[C:7]2[NH:6][CH2:5][CH2:4]1.CS(C)=[O:29].[OH-].[Na+].OO>CCO>[NH2:1][CH2:2][CH:3]1[N:8]2[N:9]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)[C:11]([C:12]([NH2:13])=[O:29])=[C:7]2[NH:6][CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 136928071HCID 136928071、化合物

生成物 1

HCID 1369280997-(Aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide収率 64%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 7-(aminomethyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (15 mg, 0.043 mmol) in 2 mL of EtOH was added 1 mL of DMSO, 0.5 mL of NaOH (5N) and 0.5 mL of H2O2 (30% aqueous solution). After stirring at 60° C. for 2 hr, the mixture was concentrated to remove EtOH. The residue was partitioned between water (30 mL) and EA (20 mL). The organic phase was concentrated and purified by pre-HPLC eluting from 20% to 40% CH3CN in 0.1% TFA in H2O. Fractions containing the desired product were combined and lyophilized overnight to give the product as a TFA salt (10 mg, 64%). 1H NMR (400 MHz, DMSO-d6) δ 8.07 (br s, 3H), 7.62 (d, J=8.8 Hz, 2H), 7.43-7.35 (m, 2H), 7.25 (t, J=7.6 Hz, 1H), 7.15-7.12 (m, 4H), 6.77 (br s, 1H), 4.38-4.30 (m, 1H), 3.40-3.20 (m, 4H), 2.16-2.06 (m, 1H), 2.00-1.80 (m, 1H). MS (ESI) m/e [M+1]+364.0.

後処理

  1. concentrationthe mixture was concentrated
  2. customto remove EtOH
  3. customThe residue was partitioned between water (30 mL) and EA (20 mL)
  4. concentrationThe organic phase was concentrated
  5. custompurified
  6. washby pre-HPLC eluting from 20% to 40% CH3CN in 0.1% TFA in H2O
  7. additionFractions containing the desired product
  8. waitlyophilized overnight

出典と根拠

ORDレコード
ord-4434afa9eac44a7d8209931b9f813b14
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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