Aluminium lithium hydride → 1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-N-methyl-1H-benzimidazol-5-amine

HRID 1796513Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([NH:14][C:15](=O)OC)=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([NH:14][CH3:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of methyl [1-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-1H-benzimidazol-5-yl]carbamate (0.781 g, 2.06 mmol) in THF was added LAH (0.32 g, 8.43 mmol) at 0° C. The mixture was stirred for 1 h at 0° C. and 2.5 h at reflux, cooled town to −78° C., and quenched with MeOH (5 mL) and H2O (5 mL). After adding Na2SO4 (10 g), the resulting mixture was stirred for 1 h at room temperature. After filtration and concentration, the residue was purified by MPLC using EtOAc on silica gel to give 641.7 mg (93%) of the title compound as an off-white solid. 1HNMR (CDCl3): δ 0.22 (m, 2H), 0.48 (m, 2H), 1.26 (m, 1H), 1.38 (t, J=7.0 Hz, 3H), 2.89 (s, 3H), 3.83 (d, J=6.6 Hz, 2H), 3.98 (q, J=7.0 Hz, 2H), 4.23 (s, 2H), 6.64 (dd, J=8.6, 2.2 Hz, 1H), 6.80 (d, J=8.6 Hz, 2H), 6.99 (d, J=2.1 Hz, 1H), 7.13 (m, 3H). MS (ESI) (M+H)+=336.42.

Workup

temperatureat reflux
temperaturecooled town to −78° C.
customquenched with MeOH (5 mL) and H2O (5 mL)
additionAfter adding Na2SO4 (10 g)
stirringthe resulting mixture was stirred for 1 h at room temperature
filtrationAfter filtration and concentration
customthe residue was purified by MPLC

Sources & evidence

ORD record: ord-73cc297bfabe425a8322d56d260922ca
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030139B2

Reaction notes

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