Ammonium Hydroxide → HCID 178461773, compound

HRID 1424153Notes

Reaction equation

HRID 1424153 reaction equation
[OH-].[NH4+:2].C(OC([NH:10][C@H:11]([C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[C:28]([F:34])[CH:27]=3)=[CH:25][C:19]=2[N:18]=1)[C@@H:12]([CH3:16])[C:13](O)=[O:14])=O)(C)(C)C>C(Cl)Cl.C1CCCCC1>[NH2:10][C@H:11]([C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[C:28]([F:34])[CH:27]=3)=[CH:25][C:19]=2[N:18]=1)[C@@H:12]([CH3:16])[C:13]([NH2:2])=[O:14]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 178461818HCID 178461818, compound

Product 1

HCID 178461773HCID 178461773, compound

Reagents, catalysts & solvents 1

HCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

The title compound was prepared according to Preparation 28 using ammonium hydroxide and (2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-[5-(4-cyano-3-fluorophenyl)-1H-benzimidazol-2-yl]-2-methylpropanoic acid (Preparation 32). The residue was sonicated in DCM:cyclohexane 5:1 to afford the boc protected amide intermediate. The residue was dissolved in 4M HCl in dioxane and stirred at room temperature for 3 hours. The solvent was removed in vacuo and the residue dissolved in MeOH and passed through an SCX cartridge eluting first with MeOH followed by 3M NH3 in MeOH. The residue was purified using silica gel column chromatography eluting with DCM:MeOH:NH3 (90:10:0.5) to afford the title compound (55 mg, 71%).

Sources & evidence

ORD record
ord-d79359451b6f42798077134ffd4b8b51
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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