Sodium triacetoxyborohydride → 1'-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)-3-methyl-1,3'-biazetidin-3-ol

HRID 1923281

反応式

HRID 1923281 の反応式
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]=O)[N:14]3[CH3:17])=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=2[N:4]=1)[CH3:2].[CH3:30][C:31]1([OH:39])[CH2:34][N:33]([CH:35]2[CH2:38][NH:37][CH2:36]2)[CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH2:18][N:37]4[CH2:38][CH:35]([N:33]5[CH2:34][C:31]([CH3:30])([OH:39])[CH2:32]5)[CH2:36]4)[N:14]3[CH3:17])=[C:10]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=2[N:4]=1)[CH3:2]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 552992011-(Azetidin-3-yl)-3-methylazetidin-3-olHCID 596059872-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde

生成物 1

HCID 596058721'-((2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)-3-methyl-1,3'-biazetidin-3-ol収率 89%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.092 g, 0.234 mmol), 3-methyl-[1,3′]biazetidinyl-3-ol (0.040 g, 0.28 mmol) and 4 Å molecular sieves (0.25 g) in DCE (3 mL). The reaction mixture was stirred for 90 min at room temperature. Sodium triacetoxyborohydride (0.099 g, 0.47 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The suspension was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 10:90) to give 587 as a white solid (0.107 g, 89%). LCMS (Method I): RT=2.33 min, [M+H]+ 518.2 1H NMR (300 MHz, DMSO-d6): δ 8.03-7.99 (m, 1 H), 7.65-7.61 (m, 1 H), 7.27-7.22 (m, 2 H), 4.49-3.95 (m, 4 H), 3.84 (s, 2 H), 3.80-3.74 (m, 4 H),3.36-3.31 (s, 3 H), 3.31-3.20 (m, 6 H), 3.11-3.01 (m, 4 H), 2.98-2.93 (m, 2 H), 1.34 (m, 5 H)

後処理

  1. stirringthe reaction mixture was stirred for 18 h at room temperature
  2. filtrationThe suspension was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 10:90)

出典と根拠

ORDレコード
ord-4498b1705de84165b0af71a3cdb21cf8
出典データセット
uspto-grants-2012_05
特許番号
US08173650B2

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