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Sodium triacetoxyborohydride → 2-(4-tert-butylphenyl)-7-(4-((2-ethyl-5-methyl-1H-imidazol-4-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-c]pyridine

HRID 729356
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HRID 729356 반응식
C(O[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[N:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=4)[NH:23][C:19]=3[CH:20]=[N:21][CH:22]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[CH2:36]([C:38]1[NH:42][C:41](C=O)=[C:40]([CH3:45])[N:39]=1)[CH3:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.[Pd]>[C:32]([C:29]1[CH:30]=[CH:31][C:26]([C:24]2[NH:25][C:18]3[C:17]([N:14]4[CH2:15][CH2:16][N:11]([CH2:9][C:41]5[NH:42][C:38]([CH2:36][CH3:37])=[N:39][C:40]=5[CH3:45])[CH2:12][CH2:13]4)=[CH:22][N:21]=[CH:20][C:19]=3[N:23]=2)=[CH:27][CH:28]=1)([CH3:34])([CH3:33])[CH3:35]
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참가 물질

6

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 578327604-[2-(4-tert-Butyl-phenyl)-3H-imidazo[4,5-c]pyridin-7-yl]-piperazine-1-carboxylic acid benzyl esterHCID 178437630HCID 178437630, 화합물

생성물 1

HCID 1784376222-(4-tert-butylphenyl)-7-(4-((2-ethyl-5-methyl-1H-imidazol-4-yl)methyl)piperazin-1-yl)-3H-imidazo[4,5-c]pyridine수율 34.6%

시약·촉매·용매 2

HCID 23938
Palladium
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

4-[2-(4-tert-Butyl-phenyl)-3H-imidazo[4,5-c]pyridin-7-yl]-piperazine-1-carboxylic acid benzyl ester 7 (12 mg, 0.026 mmol) was dissolved in THF (2 ml) with 10% Pd/C (10 mg) and allowed to stir under a hydrogen atmosphere for 12 hours. The reaction was judged complete by MS. 2-Ethyl-5-methyl-3H-imidazole-4-carbaldehyde 8 (7 mg, 0.05 mmol) and sodium triacetoxyborohydride (15 mg. 0.072 mmol) were added, and the reaction was allowed to stir for 12 hours. It was judged complete by MS, and the crude was purified by HPLC (Method E) to yield the title product 9 (4 mg (25%), 0.009 mmol). 1H NMR (CD3OD-d4): δ 8.58 (s, 1H), 8.12 (d, J=8.6 Hz, 2H), 7.72 (s, 1H), 7.58 (d, J=8.6 Hz, 2H), 3.93 (m, 5H), 3.25 (s, 3H), 3.05 (m, 3H), 2.79 (q, J=7.4 Hz, 2H), 1.35 (s, 9H). MS (ESI-POS): [M+H]+=458; MS (ESI-NEG):[M−H]−=456.

후처리

  1. stirringto stir for 12 hours
  2. customthe crude was purified by HPLC (Method E)

출처 및 근거

ORD 기록
ord-dd293431d1b74e90acee1697fe5c153d
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07582634B2

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