Isopropylamine → N-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl)propan-2-amine

HRID 1806364노트

반응식

HRID 1806364 반응식
C1(C[NH:5][CH2:6][C:7]2[CH:8]=[N:9][CH:10]=[C:11]([B:13]3[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]3)[CH:12]=2)CC1.C(S(N1CC[CH:30](C2C3C(=C(C(N)=O)C=C(C4C=NC=C(CNC(C)C)C=4)C=3)NC=2)[CH2:29][CH2:28]1)(=O)=O)C.C(N)(C)C.CC1(C)C(C)(C)OB(C2C=C(C=O)C=NC=2)O1.[BH3-]C#N.[Na+]>CO>[CH3:28][CH:29]([NH:5][CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([B:13]2[O:17][C:16]([CH3:18])([CH3:19])[C:15]([CH3:20])([CH3:21])[O:14]2)[CH:12]=1)[CH3:30]

참가 물질

7

반응물 5

HCID 6363IsopropylamineHCID 49926405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 574157101-cyclopropyl-N-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl)methanamineHCID 577327213-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(1-methylethyl)amino]methyl}-3-pyridinyl)-1H-indole-7-carboxamide

생성물 1

HCID 57415713N-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl)propan-2-amine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The (cyclopropyl methyl){[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methyl}amine used to prepare 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(1-methylethyl)amino]methyl}-3-pyridinyl)-1H-indole-7-carboxamide was prepared as follows: isopropylamine (0.011 mL, 0.129 mmol) was added to a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinecarbaldehyde (30 mg, 0.129 mmol) in MeOH (1 mL) in a 2-dram vial. NaCNBH3 (16 mg, 0.258 mmol) was then added, the vial was capped and the reaction was stirred at room temperature for 24 h. The reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL MeOH), eluting in sequence with MeOH (6 mL) and a 2 M solution of NH3/MeOH (9 mL). The NH3/MeOH fraction was concentrated under a stream of nitrogen to give 22 mg of crude (1-methylethyl){[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methyl}amine.

후처리

  1. customwas prepared
  2. customthe vial was capped
  3. filtrationThe reaction mixture was filtered through a 2 g SCX cartridge (pre-equilibrated with 3 mL MeOH)
  4. washeluting in sequence with MeOH (6 mL)
  5. concentrationThe NH3/MeOH fraction was concentrated under a stream of nitrogen

출처 및 근거

ORD 기록
ord-d031797d2c854c50928055fbd9750ead
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354406B2

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