Hydrochloric Acid → HCID 178496986, compound

HRID 1898350Notes

Reaction equation

HRID 1898350 reaction equation
[NH2:1][C:2]1[C:7]2[NH:8][C:9]([NH:11][C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[C:4]([C:20]([O:22][CH3:23])=[O:21])[C:3]=1[OH:24].Cl.[CH:26]1([C:29](=N)OCC)[CH2:28][CH2:27]1>C(Cl)Cl>[CH:26]1([C:29]2[O:24][C:3]3[C:4]([C:20]([O:22][CH3:23])=[O:21])=[CH:5][C:6]4[N:10]=[C:9]([NH:11][C:12]5[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=5[Cl:19])[NH:8][C:7]=4[C:2]=3[N:1]=2)[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14518434Ethyl cyclopropanecarboximidateHCID 178496989HCID 178496989, compound

Product 1

HCID 178496986HCID 178496986, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

Under N2 atmosphere to a cold solution of methyl 7-amino-2-[(2,6-dichlorophenyl)amino]-6-hydroxy-1H-benzimidazole-5-carboxylate (0.400 g, 1.05 mmol) in DCM (25 mL) was added HCl salt of ethyl cyclopropanecarboximidate (Intermediate-57, 0.234 g, 1.57 mmol) at 0° C. The reaction mass was stirred at 0-5° C. for 1 h and at RT for 24 h. The obtained crude was purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH:DCM to afford 0.150 g of the desired product. (DMSO-d6): δ 1.06-1.14 (m, 4H), 3.88 (s, 3H), 2.3 (m, 1H), 7.41 (s, 1H), 7.62 (d, J=7.8 Hz, 2H), 7.69 (s, 1H), 9.47 (s, 1H), 11.55 (s, 1H).

Workup

  1. customThe obtained crude
  2. customwas purified by column chromatography on neutral alumina eluting with 1.0-2.0% MeOH

Sources & evidence

ORD record
ord-0e6ef0e6bec647c4887d81d690a27877
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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