Sodium Carbonate → Tert-butyl 4-[4-(6-amino-5-formylpyridin-3-yl)pyrazol-1-yl]-piperidine-1-carboxylate

HRID 241408노트

반응식

HRID 241408 반응식
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5](I)=[CH:4][N:3]=1.CC1(C)C(C)(C)OC([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)[CH:23]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:19]2[CH:20]=[N:21][N:22]([CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)[CH:23]=2)=[CH:6][C:7]=1[CH:8]=[O:9]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 177501772-Amino-5-iodopyridine-3-carbaldehydeHCID 67495092Tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate

생성물 1

HCID 86664806Tert-butyl 4-[4-(6-amino-5-formylpyridin-3-yl)pyrazol-1-yl]-piperidine-1-carboxylate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

150 mg (0.605 mmol) of 2-amino-5-iodopyridine-3-carbaldehyde and 413 mg (1.089 mmol) of tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate are dissolved in 2.3 ml of N,N-dimethylformamide in a nitrogen-filled microwave vessel, and 1.7 ml (3.4 mmol) of 2M sodium carbonate solution and 35 mg (0.030 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer. The reaction mixture is cooled to room temperature and filtered. The filtrate is evaporated to dryness. The oily residue is purified by means of RP-HPLC, giving tert-butyl 4-[4-(6-amino-5-formylpyridin-3-yl)pyrazol-1-yl]-piperidine-1-carboxylate; HPLC-MS [M+H]+ 372.2.

후처리

  1. additionfilled microwave vessel
  2. customThe reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer
  3. filtrationfiltered
  4. customThe filtrate is evaporated to dryness
  5. customThe oily residue is purified by means of RP-HPLC

출처 및 근거

ORD 기록
ord-22780cbc61a64bfd8fb8086c92eba15a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648201B2

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