Diisopropylethylamine → 2-tert-Butyl-5-(isoxazolidin-2-ylsulfonyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole

HRID 1435411ノート

反応式

HRID 1435411 の反応式
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21](Cl)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[O:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.CC#N>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([S:21]([N:27]3[CH2:28][CH2:29][CH2:30][O:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 12304500Isoxazolidine hydrochlorideHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

生成物 1

HCID 236592992-tert-Butyl-5-(isoxazolidin-2-ylsulfonyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole収率 36%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒

実験手順

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (61 mg, 0.17 mmol), isoxazolidine hydrochloride (44 mg, 0.40 mmol), DIPEA (0.2 mL, 149 mg, 1.15 mmol) and DMAP (50 mg, 0.41 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:1) on silica gel to give 24 mg (36%) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.43-1.61 (m, 4 H), 1.63 (s, 9 H), 2.02-2.19 (m, 2 H), 2.25-2.42 (m, 1 H), 3.29-3.38 (m, 2 H), 3.64-3.73 (m, 2 H), 3.86 (t, J=7.13 Hz, 2 H), 3.88-3.96 (m, 2 H), 4.49 (d, J=7.42 Hz, 2 H), 7.98 (d, J=1.56 Hz, 1 H), 7.99 (s, 1 H), 8.24 (d, J=0.78 Hz, 1 H); MS (ESI) (M+H)+=408.0; Anal. Calcd for C20H29N3O4S+1.20 TFA+0.20 EtOAc (561.99): C, 49.58; H, 5.70; N, 7.48. Found: C, 49.74; H, 5.53; N, 7.46.

後処理

  1. customThe crude product was purified by MPLC

出典と根拠

ORDレコード
ord-32319cf851b34cb1a4a45ea50f73b28c
出典データセット
uspto-grants-2009_11
特許番号
US07615642B2

反応ノート

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