Water → HCID 178491329, compound

A stirred solution of methyl 2-cyclopropyl-7-methoxy-3 H-benzimidazole-4-carboxylate, in dry tetrahydrofuran (220 ml), at −78° C. and under nitrogen, was treated dropwise over 3 hours with a solution of diisobutylaluminium hydride in dichloromethane (270 ml, 1.0M). The reaction mixture was allowed to warm to room temperature over 30 minutes, then cooled to −78° C., then treated dropwise with water (27 ml), then allowed to warm to room temperature. The reaction mixture was diluted with ice-water (500 ml) and the pH of the mixture was adjusted to above 12 by the addition of aqueous sodium hydroxide (750 ml, 1M). The resulting white suspension was filtered to yield a clear filtrate which was extracted seven times with ethyl acetate (500 ml): The combined extracts were dried over magnesium sulphate and then evaporated to yield the title compound as a cream coloured powder (10.13 g).

1. temperaturecooled to −78° C.
2. temperatureto warm to room temperature
3. filtrationThe resulting white suspension was filtered
4. customto yield a clear filtrate which
5. extractionwas extracted seven times with ethyl acetate (500 ml)
6. dry with materialThe combined extracts were dried over magnesium sulphate
7. customevaporated

ORD record

ord-d14c686971ff40b69647f4b1111d0b1e

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303600B1