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Hydrochloric Acid → HCID 178434340, 화합물

HRID 1038832
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HRID 1038832 반응식
C([NH:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:12]3[O:37][CH:36]=[CH:35][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH3:34])=[N:23][N:24]4C(OC(C)(C)C)=O)=[CH:20][CH:19]=3)[N:16]=2)[CH2:7]1)(=O)C.Cl.NCC1CCN(C(OC(C)(C)C)=O)C1.C(Cl)(=O)C.ClC1N=C(Cl)C2OC=CC=2N=1.Cl>CO>[NH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[C:12]3[O:37][CH:36]=[CH:35][C:13]=3[N:14]=[C:15]([NH:17][C:18]3[CH:26]=[C:25]4[C:21]([C:22]([CH3:34])=[N:23][NH:24]4)=[CH:20][CH:19]=3)[N:16]=2)[CH2:7]1
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참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 45072187tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate hydrochlorideHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 67130041HCID 67130041, 화합물

생성물 1

HCID 178434340HCID 178434340, 화합물수율 61%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
90 °C

실험 절차

To a solution of tert-butyl 6-(4-(3-(acetamidomethyl)pyrrolidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-3-methyl-1H-indazole-1-carboxylate (0.57 g, 1.1 mmol, prepared using E.1 from tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate hydrochloride [Astatech] with acetyl chloride, C, A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with Example #3, Step B) in MeOH (12 mL) was added concentrated HCl (12 mL). The mixture was stirred for about 32 h at about 90° C. The mixture was cooled to rt, and a white precipitate formed that was collected by vacuum filtration and washed with water. The solid was dissolved in hot aqueous 1 M HCl and the suspension was filtered while hot. To the filtrate was added aqueous NH4OH to reach a pH˜9, and the resulting precipitate was collected to give 4-(3-(aminomethyl)pyrrolidin-1-yl)-N-(3-methyl-1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.27 g, 61%): LC/MS (Table 2, Method h) Rt=1.61 min; MS m/z: 364 (M+H)+. Syk IC50=A

후처리

  1. temperatureThe mixture was cooled to rt
  2. customa white precipitate formed
  3. filtrationthat was collected by vacuum filtration
  4. washwashed with water
  5. dissolutionThe solid was dissolved in hot aqueous 1 M HCl
  6. filtrationthe suspension was filtered while hot
  7. additionTo the filtrate was added aqueous NH4OH
  8. customthe resulting precipitate was collected

출처 및 근거

ORD 기록
ord-c2b96bd7d9d049508eee901b9dcc75f3
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08551981B2

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