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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
ノート
印刷プレビュー

反応式

HRID 729356 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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、化合物

生成物 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]pyridine収率 34.6%

試薬・触媒・溶媒 2

HCID 23938
Palladium
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-dd293431d1b74e90acee1697fe5c153d
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582634B2

反応ノート

読み込み中…

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