Hydrochloric Acid → HCID 9936285, compound

HRID 1376187Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([C@@:22]([NH:31][CH2:32][C:33]([OH:35])=[O:34])([C:24]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[O:25])[CH3:23])=[CH:21][C:14]=3[N:13]=2)=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].[ClH:36]>CO.C(OCC)(=O)C>[ClH:36].[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][C:20]([C@@:22]([NH:31][CH2:32][C:33]([OH:35])=[O:34])([C:24]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[O:25])[CH3:23])=[CH:21][C:14]=3[N:13]=2)=[CH:8][CH:9]=1)(=[NH:2])[NH2:3]

Participants

Conditions

Temperature: 20 °C

Procedure

A suspension of 11 g (23 mmol) of (R)-2-(4-amidinophenylaminomethyl)-1-methyl-5-[1-(carboxymethylamino)-1-(pyrrolidinocarbonyl)-ethyl]-benzimidazole in 88 mL methanol is heated to 35° C. to 40° C. To this suspension are added 8.4 mL of a 2.75 molar solution of hydrogen chloride (23 mmol) in ethyl acetate. The starting material is dissolved and the hydrochloride begins to crystallise out. The suspension is cooled to 20° C. and suction filtered. The filter cake is dried in the vacuum drying cupboard at 35° C. 9.2 g (78% of theory) of the title compound are obtained as a crystalline solid. To eliminate traces of methanol 8 g of the title compound obtained above are suspended in 80 mL of ethanol and stirred for 30 minutes at 50° C. The suspension is cooled to 20° C. and suction filtered. The filter cake is washed with ethanol and dried in the vacuum drying cupboard at 35° C.

Workup

temperatureis heated to 35° C. to 40° C
dissolutionThe starting material is dissolved
customto crystallise out
filtrationsuction filtered
customThe filter cake is dried in the vacuum
customdrying cupboard at 35° C

Sources & evidence

ORD record: ord-43a958c9197249cf9ae06d00ebfd3aca
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169934B2

Reaction notes

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