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Acetic Acid → HCID 44477250, 화합물

HRID 2361674
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HRID 2361674 반응식
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:17][CH:16]([NH:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH3:28])=[O:26])=[N:23][CH:24]=4)[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[BH3-][C:30]#N.[Na+].C(O)(=O)C>CC#N.O.C=O>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:15][CH:16]([N:18]([CH3:30])[C:19]4[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH3:28])=[O:26])=[N:23][CH:24]=4)[CH2:17]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1
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참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 44477249HCID 44477249, 화합물

생성물 1

HCID 44477250HCID 44477250, 화합물수율 19%

시약·촉매·용매 2

HCID 712Formaldehyde용매HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

5-({1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}amino)-N-methylpyridine-2-carboxamide (34 mg, 92 μmol) was dissolved in 1:1 MeCN/water (3 ml) and formaldehyde (50 μl of a 37% wt. soln, 1.8 mmol) followed by NaBH3CN (34 mg, 0.56 mmol) were added. After 10 minutes, acetic acid (40 μl, 0.72 mmol) was added and the reaction stirred at room temperature for 16 hours. The reaction mixture was concentrated at reduced pressure and purified by FCC (DCM/MeOH/NH3 gradient, 98:2:1 to 90:10:1) giving the title compound as colourless oil (7 mg, 19%).

후처리

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. custompurified by FCC (DCM/MeOH/NH3 gradient, 98:2:1 to 90:10:1)

출처 및 근거

ORD 기록
ord-400c61a7d2b14ebe990964b0e7d4f4b0
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691804B2

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