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Diisopropylethylamine → (+/-)-2-(2-Oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)-N-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2-yl)acetamide

HRID 1921229
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HRID 1921229 반응식
[O:1]=[C:2]1[N:6]([CH2:7][C:8]([OH:10])=O)[C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[N:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.[NH2:21][C:22]1[N:27]=[C:26]2[CH2:28][C:29]3([CH2:39][C:25]2=[CH:24][CH:23]=1)[C:37]1[C:32](=[N:33][CH:34]=[CH:35][CH:36]=1)[NH:31][C:30]3=[O:38].C1CN(C(Cl)=[N+]2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[O:1]=[C:2]1[N:6]([CH2:7][C:8]([NH:21][C:22]2[N:27]=[C:26]3[CH2:28][C:29]4([CH2:39][C:25]3=[CH:24][CH:23]=2)[C:37]2[C:32](=[N:33][CH:34]=[CH:35][CH:36]=2)[NH:31][C:30]4=[O:38])=[O:10])[C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[N:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27366521-(Chloro-1-pyrrolidinylmethylene)pyrrolidinium HexafluorophosphateHCID 18449368(2-Oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)acetic acid2회HCID 57974056(+/-)-2-Amino-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

생성물 1

HCID 25143873
(+/-)-2-(2-Oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)-N-(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2-yl)acetamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (2-oxo-3-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-1-yl)acetic acid (16 mg, 0.060 mmol, described in Intermediate 7), (±)-2-amino-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1W)-one (15 mg, 0.060 mmol, described in Intermediate 5), PyClu (26 mg, 0.072 mmol), and DIEA (0.053 mL, 0.30 mmol) in THF (1 mL) was stirred at ambient temperature for 18 h. The reaction mixture was purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=504 (M+1). HRMS: m/z=504.1796; calculated m/z=504.1779 for C28H22N7O3.

후처리

  1. customThe reaction mixture was purified directly by HPLC
  2. washeluting with a gradient of H2O

출처 및 근거

ORD 기록
ord-220097cf23f04e578c26a45773a34ab1
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173655B2

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