Diisopropylethylamine → methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)cyclohexanecarboxylate

HRID 530875노트

반응식

HRID 530875 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=O)[CH:15]=3)[N:10]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:39][CH:40]1[CH2:45][CH2:44][CH2:43][C:42]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=2)([C:46]([O:48][CH3:49])=[O:47])[CH2:41]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:57][C:54]1[CH:53]=[CH:52][C:51]([CH2:50][C:42]2([C:46]([O:48][CH3:49])=[O:47])[CH2:43][CH2:44][CH2:45][CH:40]([NH:39][C:17]([C:14]3[CH:15]=[C:16]4[C:11](=[CH:12][CH:13]=3)[N:10]([C:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:9]=[C:8]4[C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)=[O:19])[CH2:41]2)=[CH:56][CH:55]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67983392Methyl 3-amino-1-(4-fluorobenzyl)cyclohexanecarboxylateHCID 679849753-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid

생성물 1

HCID 67985845methyl 1-(4-fluorobenzyl)-3-(3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxamido)cyclohexanecarboxylate수율 85.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a flask, 3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carboxylic acid (567 mg, 1.15 mmol), methyl 3-amino-1-(4-fluorobenzyl)cyclohexanecarboxylate (1.09 mmol), and HATU (622 mg, 1.64 mmol) was dissolved in dimethylformamide (3 mL). The reaction mixture was stirred for 2 minutes at room temperature. Diisopropylethylamine (0.95 mL, 5.45 mmol) was added to the reaction. The reaction was allowed to stir for an additional 1 hr. Upon completion, the reaction was quenched with water (5 mL). The water layer was extracted with ethyl acetate (20 mL) three times. The organic fractions were combined, dried with sodium sulfate, and concentrated to yield the crude product. The crude compound was purified using flash chromatography (0-100% ethyl acetate in hexane gradient) to give the title compound (690 mg).

후처리

  1. stirringto stir for an additional 1 hr
  2. customUpon completion, the reaction was quenched with water (5 mL)
  3. extractionThe water layer was extracted with ethyl acetate (20 mL) three times
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customto yield the crude product
  7. customThe crude compound was purified

출처 및 근거

ORD 기록
ord-181dd0956820485987ff188e2a5d952a
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09351965B2

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