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Dichloromethane → 2-Amino-4-methyl-6-((S)-1-(1-methyl-6-((S)-3-(methylamino)pyrrolidin-1-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethylamino)pyrimidine-5-carbonitrile

HRID 2205617
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HRID 2205617 반응식
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[N:16]=[C:15]3[CH:17]=[CH:18][N:19]([CH3:20])[C:14]3=[CH:13][C:12]=2[N:21]2[CH2:25][CH2:24][C@H:23]([N:26](C)[C:27](=O)OC(C)(C)C)[CH2:22]2)[CH3:10])[C:5]([C:35]#[N:36])=[C:4]([CH3:37])[N:3]=1.C(O)(C(F)(F)F)=O.[Cl:45]CCl>>[ClH:45].[NH2:1][C:2]1[N:3]=[C:4]([CH3:37])[C:5]([C:35]#[N:36])=[C:6]([NH:8][C@H:9]([C:11]2[N:16]=[C:15]3[CH:17]=[CH:18][N:19]([CH3:20])[C:14]3=[CH:13][C:12]=2[N:21]2[CH2:25][CH2:24][C@H:23]([NH:26][CH3:27])[CH2:22]2)[CH3:10])[N:7]=1
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참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 118214739tert-Butyl ((S)-1-(5-((S)-1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidin-3-yl)(methyl)carbamate

생성물 2

HCID 313Hydrochloric AcidHCID 1182077992-Amino-4-methyl-6-((S)-1-(1-methyl-6-((S)-3-(methylamino)pyrrolidin-1-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethylamino)pyrimidine-5-carbonitrile
수율 84%

실험 절차

To a 25 mL pear flask was added tert-butyl ((S)-1-(5-((S)-1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidin-3-yl)(methyl)carbamate (61 mg, 0.121 mmol) in dichloromethane (0.8 mL) to give a solution. To this solution was added TFA (0.27 mL), and the mixture was stirred at room temperature for 18 hours. All the volatiles were removed in vacuo, and the residue was re-suspended in toluene and concentrated to remove residual TFA. The residue was then diluted in ACN and water (total of about 90 mL), followed by the addition of 2 N HCl (4 mL). The mixture was then lyophilized to give an HCl salt of the title compound as a yellow-green solid (41 mg, 84%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.66 (d, J=6.82 Hz, 2H), 2.17 (td, J=12.69, 7.20 Hz, 1H), 2.31-2.45 (m, 3H), 2.61 (s, 2H), 3.20-3.39 (m, 2H), 3.46 (br s, 1H), 3.57 (br s, 1H), 3.95 (s, 3H), 5.91 (t, J=6.95 Hz, 1H), 6.79 (br s, 1H), 7.68 (br s, 1H), 8.03 (br s, 1H), 8.48 (br s, 1H), 8.77 (br s, 1H), 9.32-9.50 (m, 1H), 9.60-9.82 (m, 1H); ESI-MS m/z [M+H]+ calc'd for C21H27N9, 406. found 406.

후처리

  1. customto give a solution
  2. customAll the volatiles were removed in vacuo
  3. concentrationconcentrated
  4. customto remove residual TFA
  5. additionThe residue was then diluted in ACN
  6. additionwater (total of about 90 mL), followed by the addition of 2 N HCl (4 mL)

출처 및 근거

ORD 기록
ord-f4a7f2d4be6949d8b14b8be5190da671
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09371321B2

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