Hydrochloric Acid → EOS-62353

HRID 875703ノート

反応式

HRID 875703 の反応式
[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

参加物

6

反応物 2

HCID 313Hydrochloric AcidHCID 67045318HCID 67045318、化合物

生成物 1

HCID 67045163EOS-62353収率 67%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-e978635baa2d4d4685b3c626ce4bf1fa
出典データセット
uspto-grants-2015_03
特許番号
US08981085B2

反応ノート

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