N-[2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]acetamide → 2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-amine

HRID 1435409Notes

Reaction equation

[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]([NH:21]C(=O)C)=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2]>Cl>[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]([NH2:21])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 95 °C

Procedure

N-[2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]acetamide (20.7 g, 62.8 mmol) was dissolved in 37% HCl (120 mL). The solution was heated at 95° C. for 20 h. After concentration, 20.4 g (100%) of a purple solid was obtained. 1H NMR (400 MHz, CHLOROFORM-D) δ 1.47-1.52 (m, 4 H), 1.54 (s, 9 H), 2.23-2.31 (m, 1 H), 3.28-3.36 (m, 2 H), 3.96 (t, J=3.12 Hz, 1 H), 3.97-4.00 (m, 1 H), 4.13 (d, J=7.62 Hz, 2 H), 6.66 (dd, J=8.40, 2.15 Hz, 1 H), 7.06 (d, J=2.15 Hz, 1 H), 7.10 (d, J=8.40 Hz, 1 H); MS (ESI) (M+H)+=288.0.

Workup

concentrationAfter concentration

Sources & evidence

ORD record: ord-f5bbae4a046143018aac1608dc989bfa
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615642B2

Reaction notes

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