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Diisopropylethylamine → (R,E)-1-(3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)-4-(cyclobutyl(methyl)amino)but-2-en-1-one

HRID 920201
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HRID 920201 반응식
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([C@@H:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[N:3]=1.Cl.[CH:18]1([N:22]([CH3:29])[CH2:23]/[CH:24]=[CH:25]/[C:26](O)=[O:27])[CH2:21][CH2:20][CH2:19]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([C@@H:12]3[CH2:16][CH2:15][N:14]([C:26](=[O:27])/[CH:25]=[CH:24]/[CH2:23][N:22]([CH:18]4[CH2:21][CH2:20][CH2:19]4)[CH3:29])[CH2:13]3)[N:3]=[C:2]([I:1])[C:10]=12
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71209048(E)-4-(cyclobutyl(methyl)amino)but-2-enoic acid hydrochlorideHCID 71256207(R)-3-iodo-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

생성물 1

HCID 71256082
(R,E)-1-(3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)-4-(cyclobutyl(methyl)amino)but-2-en-1-one
수율 118.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a cooled solution of (R)-3-iodo-1-(pyrrolidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (4) (990 mg, 3.0 mmol), (E)-4-(cyclobutyl(methyl)amino)but-2-enoic acid (21) (871 mg, 3.0 mmol) and DIPEA (3.1 mL, 18 mmol) in DMF (15 mL) was added HBTU (1.74 g, 4.5 mmol). The resulting solution was stirred at RT overnight, then quenched with water. The layers were separated and the aqueous layer was extracted with 85% DCM/IPA(3×). The combined organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography to provided (R,E)-1-(3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)-4-(cyclobutyl(methyl)amino)but-2-en-1-one (22) (1.71 g, quant. yield) as a white solid. LC-MS (ESI): m/z (M+1) 482.0.

후처리

  1. customquenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 85% DCM/IPA(3×)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-ae310f25cc3b42c3b4c5cc6236da075b
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273051B2

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