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Diisopropylethylamine → N-(4-ethynylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 530963
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HRID 530963 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[N:9]=[CH:10][C:11]([C:12]([OH:14])=O)=[C:4]2[N:3]=1.[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)#[CH:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:15]([C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:12]([C:11]2[CH:10]=[N:9][N:5]3[C:6]([CH3:8])=[CH:7][C:2]([CH3:1])=[N:3][C:4]=23)=[O:14])=[CH:19][CH:18]=1)#[CH:16]
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 7440385,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 37600254-EthynylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 46907762N-(4-ethynylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide
수율 46%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid (722 mg, 3.78 mmol), 4-ethynylaniline (442 mg, 3.78 mmol), and HATU (1436 mg, 3.78 mmol) were taken up in DMF (10 ml) and then treated with diisopropylethylamine (1.979 ml, 11.33 mmol). The contents stirred at room temperature overnight. The product had precipitated from reaction mixture. The reaction was diluted with water, filtered through a Büchner funnel under house vacuum. The residue was washed with water (×2), then CH2Cl2, diethyl ether, and air dried to obtain N-(4-ethynylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide (500 mg, 1.72 mmol, 46% yield). LC-MS: rt (min)=3.65. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.71 (s, 3H), 2.77 (s, 3H), 4.11 (s, 1H), 7.21 (s, 1H), 7.49 (d, J=8.6 Hz, 2H), 7.77 (d, J=8.6 Hz, 2H), 8.65 (s, 1H), 10.31 (s, 1H).

후처리

  1. customThe product had precipitated from reaction mixture
  2. additionThe reaction was diluted with water
  3. filtrationfiltered through a Büchner funnel under house vacuum
  4. washThe residue was washed with water (×2)
  5. dry with materialCH2Cl2, diethyl ether, and air dried

출처 및 근거

ORD 기록
ord-d69c47c3d9c1473abaa0ea5bdc4defae
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353117B2

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