Sodium Carbonate → 4-((1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-1H-pyrazole-1-carboxamide

HRID 594974노트

반응식

HRID 594974 반응식
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([NH:14][C:15]3[CH:16]=[N:17][NH:18][CH:19]=3)=[N:12][CH:13]=[C:8]2[CH:7]=[N:6]1.[O-:24][C:25]#[N:26].[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([NH:14][C:15]3[CH:19]=[N:18][N:17]([C:25]([NH2:26])=[O:24])[CH:16]=3)=[N:12][CH:13]=[C:8]2[CH:7]=[N:6]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 11378442Potassium cyanateHCID 67112034HCID 67112034, 화합물

생성물 1

HCID 529132844-((1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-1H-pyrazole-1-carboxamide

시약·촉매·용매 1

HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

To a solution of 1-(2-fluorobenzyl)-N-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (Example 88), (111 mg, 0.36 mmol) in ACN/H2O (9:1, 4 mL) was added potassium cyanate (35 mg, 1.2 eq). After 30 min at rt, the reaction mixture was neutralized with saturated sodium carbonate and the aqueous phase extracted with DCM. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC to give the title product. 1H NMR (d6-DMSO) δ 10.12 (s, 1H), 9.00 (s, 1H), 8.57 (s, 1H), 8.12 (s, 1H), 7.94 (s, 1H), 7.80 (s, 1H), 7.71 (s, 1H), 7.41-7.28 (m, 2H), 7.26-7.14 (m, 2H), 5.58 (s, 2H); LC-MS method B, (ES+) 353.0, RT=7.75 min.

후처리

  1. extractionthe aqueous phase extracted with DCM
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-f912df6f54814e00a83cd8188dfd8b47
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242987B2

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