1,2-Dichloroethane → 2-[(6S)-6-(3,5-Difluorophenyl)-3,3-dimethyl-2-oxopiperidin-1-yl]-N-((2R)-2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]acetamide

HRID 1866729노트

반응식

HRID 1866729 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([OH:18])=O)[C:13](=[O:19])[C:12]([CH3:21])([CH3:20])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:46](=[CH:47][CH:48]=1)[CH2:45][C@:27]1([C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:28]1=[O:44])[CH2:26]2.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([NH:22][C:23]3[CH:24]=[C:25]4[C:46](=[CH:47][CH:48]=3)[CH2:45][C@:27]3([C:35]5[C:30](=[N:31][CH:32]=[CH:33][CH:34]=5)[N:29]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:42])[CH3:43])[C:28]3=[O:44])[CH2:26]4)=[O:18])[C:13](=[O:19])[C:12]([CH3:21])([CH3:20])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 66973553[(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2-oxopiperidin-1-yl]acetic acid2회HCID 66973634(R)-5-amino-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2회

생성물 1

HCID 669731272-[(6S)-6-(3,5-Difluorophenyl)-3,3-dimethyl-2-oxopiperidin-1-yl]-N-((2R)-2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]acetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of [(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2-oxopiperidin-1-yl]acetic acid (21 mg, 0.07 mmol, described in Intermediate 49), (R)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (26 mg, 0.07 mmol, described in Intermediate 9, step B), HOBT (15 mg, 0.10 mmol), and EDC (19 mg, 0.10 mmol) in DMF (0.5 mL) was stirred at ambient temperature for 18 h. The reaction mixture was partitioned between saturated aqueous NaHCO3 (10 mL) and EtOAc (20 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=661 (M+1).

후처리

  1. customThe reaction mixture was partitioned between saturated aqueous NaHCO3 (10 mL) and EtOAc (20 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5875226e47bd4a38a3eff3836ea6f58b
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629338B2

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