Hydrochloric Acid → HCID 178428861, compound

HRID 415049Notes

Reaction equation

HRID 415049 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[N:14]=[CH:15][NH:16][C:17]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29]2)=[CH:23][C:22]=1[CH3:39])=[O:19])=[O:12].Cl>C(OCC)(=O)C.O1CCOCC1>[NH:30]1[CH2:31][CH:28]([O:27][C:24]2[CH:25]=[CH:26][C:21]([NH:20][C:18]([C:17]3[NH:16][CH:15]=[N:14][C:13]=3[C:11]([NH:10][C:2]3[NH:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[O:12])=[O:19])=[C:22]([CH3:39])[CH:23]=2)[CH2:29]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178428864HCID 178428864, compound

Product 1

HCID 178428861HCID 178428861, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl 3-({4-[({4-[(1H-benzimidazol-2-ylamino)carbonyl]-1H-imidazol-5-yl}carbonyl)amino]-3-methylphenyl}oxy)azetidine-1-carboxylate (155.0 mg, 0.29 mmol) was suspended in 5 mL of ethyl acetate, which was cooled with an ice-water bath. 3 mL of 4 N HCl in dioxane was added dropwise. The reaction mixture was stirred overnight. The suspension was filtered and the solid was washed with 5 mL of ethyl acetate, dried under vacuum to afford the desired product (102 mg, 0.22 mmol) as the hydrochloride salt. 1H-NMR (400 MHz, DMSO-d6): δ=10.9 (br, 1H), 9.85 (br, 2H), 8.32 (s, 1H), 7.63 (m, 2H), 7.38 (m, 3H), 6.84 (m, 1H), 6.78 (m, 1H), 5.05 (m, 1H), 4.43 (m, 2H), 3.94 (m, 2H), 2.25 (s, 3H). MS: 432 (M++1).

Workup

  1. temperaturewhich was cooled with an ice-water bath
  2. filtrationThe suspension was filtered
  3. washthe solid was washed with 5 mL of ethyl acetate
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7c216d5050df44eb9b099f0f43d26c85
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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