Sodium Hydroxide → HCID 178505010, compound

HRID 983795Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([C:15]3[NH:19][C:18]4[CH:20]=[CH:21][C:22]([C:24]([NH2:26])=[NH:25])=[CH:23][C:17]=4[N:16]=3)[C:9]=2[OH:27])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C1COCC1.O>[Cl:14][C:12]1[CH:11]=[C:10]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([C:24]([NH2:26])=[NH:25])=[CH:23][C:17]=3[N:16]=2)[C:9]([OH:27])=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])[CH:3]=2)[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-(3′-Amino-5-chloro-2-hydroxy-biphenyl-3-yl)-1H-benzoimidazole-5-carboxamidine 73 (0.070 g, 0.15 mmol) and THF/water (1:1, 0.5 mL) is chilled (0° C.) and treated with 2 N NaOH (0.16 mL, 0.32 mmol) and methane sulfonyl chloride (0.013 mL, 0.16 mmol) in alternating portions. The mixture is kept at 0° C. for 1 h and then treated with another portion of 2 N NaOH (0.016 mL, 0.032 mmol) and methane sulfonyl chloride (0.001 mL, 0.013 mmol). After another 1 h, the solvents were reduced in volume under reduced pressure, and the crude material is purified by C18 reversed-phase HPLC (2-65% MeCN/H2O containing 20 mM HCl, over 50 min.). The appropriate fractions were pooled and the solvent is removed under reduced pressure. 2-(5-chloro-2-hydroxy-3′-methanesulfonylamino-biphenyl-3-yl)-1H-benzoimidazole-5-carboxamidine 74 is obtained as a tan powder (0.012 g, 16% yield) (Example 288, Table 2a):

Workup

waitAfter another 1 h
customthe crude material is purified by C18 reversed-phase HPLC (2-65% MeCN/H2O containing 20 mM HCl, over 50 min.)
customthe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-3a2250bff0fe44c7b94b64c96dc42142
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867200B1

Reaction notes

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