Lithium borohydride → N-(4-(8-(Hydroxymethyl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl)benzamide

HRID 1029231

반응식

HRID 1029231 반응식
[BH4-].[Li+].[C:3]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[CH:28]=[CH:27][N:26]=[C:25]3[C:20]=2[C:21]2[CH:33]=[CH:32][C:31]([C:34](OC)=[O:35])=[CH:30][C:22]=2[C:23](=[O:29])[NH:24]3)=[CH:14][CH:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1>[OH:35][CH2:34][C:31]1[CH:32]=[CH:33][C:21]2[C:20]3[C:25](=[N:26][CH:27]=[CH:28][C:19]=3[NH:18][C:15]3[CH:14]=[CH:13][C:12]([NH:11][C:3](=[O:10])[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)=[CH:17][CH:16]=3)[NH:24][C:23](=[O:29])[C:22]=2[CH:30]=1

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 44205292Methyl 1-(4-benzamidophenylamino)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridine-8-carboxylate

생성물 1

HCID 58168103N-(4-(8-(Hydroxymethyl)-6-oxo-5,6-dihydrobenzo[c][1,8]naphthyridin-1-ylamino)phenyl)benzamide수율 31%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium borohydride (33 mg, 1.51 mmol) was added to a stirred solution of 267 (100 mg, 0.22 mmol) in THF (10 mL) at 0° C., and stirred for 20 min. at room temperature, then overnight at 45° C. The reaction solution was quenched with MeOH and H2O, acidified with HCl (1 mL, conc.), and stirred for 20 min. The crude product was purified via HP-LC to provide 273 (29 mg, 31% yield) as a solid. LC-MS (M+H=437, obsd.=437).

후처리

  1. customovernight
  2. customat 45° C
  3. customThe reaction solution was quenched with MeOH and H2O
  4. stirringstirred for 20 min
  5. customThe crude product was purified via HP-LC

출처 및 근거

ORD 기록
ord-432894fb771a4c32b94a39ed2c919576
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735584B2

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