Hydrochloric Acid → EOS-62353

HRID 875703노트

반응식

HRID 875703 반응식
[Br:1][C:2]1[C:3]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23]C(=O)OC(C)(C)C)[CH2:18]2)=[C:4]2[C:10]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[ClH:31]>C(O)(C(F)(F)F)=O.C(Cl)Cl.CCOCC>[ClH:31].[NH2:23][C@@H:19]1[CH2:20][CH2:21][CH2:22][N:17]([C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]3[NH:8][CH:9]=[C:10]([NH:11][C:12]([CH:14]4[CH2:15][CH2:16]4)=[O:13])[C:4]=23)[CH2:18]1

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 67045318HCID 67045318, 화합물

생성물 1

HCID 67045163EOS-62353수율 67%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

(R)-tert-Butyl 1-(5-bromo-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (110 mg, 0.230 mmol) in TFA (5 mL) was stirred at room temperature for 30 minutes, and the TFA was removed in vacuo. The oily residue obtained was dissolved in CH2Cl2 (1 mL), and 2M HCl in Et2O was added. The mixture was stirred at ambient temperature for 30 minutes. The solid formed was filtered and triturated with CH3CN to provide (R)—N-(4-(3-aminopiperidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide hydrochloride (70 mg, 67% yield). 1H NMR (400 MHz, (CD3)2SO) δ 11.82 (s, 1H), 9.65 (s, 1H), 8.26 (br s, 3H), 8.22 (s, 1H), 7.47 (s, 1H), 3.46-3.40 (m, 3H), 3.31-3.23 (m, 1H), 3.12-3.06 (m, 1H), 2.15-2.09 (m, 1H), 1.87-1.80 (m, 2H), 1.76-1.69 (m, 1H), 1.53-1.43 (m, 1H), 0.83-0.81 (m, 4H); LCMS (APCI+) m/z 378.8, 379.9 (M+H)+, Retention time=2.18 minutes (Method 2).

후처리

  1. customthe TFA was removed in vacuo
  2. customThe oily residue obtained
  3. customThe solid formed
  4. filtrationwas filtered
  5. customtriturated with CH3CN

출처 및 근거

ORD 기록
ord-e978635baa2d4d4685b3c626ce4bf1fa
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981085B2

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