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

HRID 64295노트

반응식

HRID 64295 반응식
[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

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 136928071HCID 136928071, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4434afa9eac44a7d8209931b9f813b14
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447106B2

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