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Cyclobutylamine → 2-tert-Butyl-N-cyclobutyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonamide

HRID 1435414
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HRID 1435414 반응식
[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].[CH:25]1([NH2:29])[CH2:28][CH2:27][CH2:26]1>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]([NH:29][CH:25]3[CH2:28][CH2:27][CH2:26]3)(=[O:23])=[O:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 2

HCID 75645CyclobutylamineHCID 579372982-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride

생성물 1

HCID 236593022-tert-Butyl-N-cyclobutyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

실험 절차

Following the same procedure in Example 1, Step A, using 2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazole-5-sulfonyl chloride (76 mg, 0.20 mmol), cyclobutylamine (43 uL, 36 mg, 0.50 mmol) and DMAP (82 mg, 0.67 mmol) in MeCN (5 mL). The crude product was purified by MPLC using Hex/EtOAc (1:2) on silica gel to give 35 mg (42% yield) of a white solid as the title compound. 1H NMR (400 MHz, METHANOL-D4) δ 1.48-1.66 (m, 6 H), 1.68 (s, 9 H), 1.72-1.87 (m, 2 H), 1.95-2.08 (m, 2 H), 2.28-2.50 (m, 1 H), 3.31-3.41 (m, 2 H), 3.68-3.83 (m, 1 H), 3.90-3.99 (m, 2 H), 4.53 (d, J=7.62 Hz, 2 H), 7.96 (dd, J=8.80, 1.6 Hz, 1 H), 8.04 (d, J=9.0 Hz, 1 H), 8.19 (d, J=1.17 Hz, 1 H); MS (ESI) (M+H)+=406.0; Anal. Calcd for C21H31N3O3S+1.20 TFA+0.60 EtOAc+0.2H2O (598.86): C, 51.75; H, 6.29; N, 7.02. Found: C, 51.70; H, 6.25; N, 7.03.

후처리

  1. customThe crude product was purified by MPLC

출처 및 근거

ORD 기록
ord-bb44fd3c496c4aefbb388063c50321ec
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07615642B2

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