Hydrochloric Acid → HCID 178511225, compound

HRID 1713774Notes

Reaction equation

HRID 1713774 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[O:14][C:13]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C@H:24]3[CH2:29][CH2:28][C@H:27]([CH2:30][NH:31]C(=O)OC(C)(C)C)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[O:16])=[N:12][N:11]=1>O1CCOCC1>[NH2:31][CH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([C:21]2[CH:20]=[CH:19][C:18]([NH:17][C:15]([C:13]3[O:14][C:10]([NH:9][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[F:2])=[N:11][N:12]=3)=[O:16])=[CH:23][CH:22]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178453587HCID 178453587, compound

Product 1

HCID 178511225HCID 178511225, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M HCl in 1,4-dioxane (1 mL) was added to tert-butyl [(trans-4-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]phenyl}cyclohexyl)-methyl]carbamate (Example 618) (50 mg, 0.10 mmol) and the suspension stirred for 18 hours. All volatiles were removed in vacuo and the residue triturated with Et2O (3 mL), the solid filtered, washed with Et2O (2×5 mL), isohexane (2×5 mL) to give the title compound (as a hydrochloride salt) (44 mg, 99%) as a white solid; 1H NMR δ 1.07-1.16 (2H, m), 1.39-1.47 (2H, m), 1.57-1.69 (1H, m), 1.87 (4H, t), 2.41-2.52 (1H, m), 2.71 (2H, d), 7.14-7.20 (1H, m), 7.23 (1H, s), 7.25-7.27 (2H, m), 7.29-7.34 (1H, m), 7.70 (2H, d), 7.87 (3H, s), 8.01-8.06 (1H, m), 10.76 (1H, s), 10.94 (1H, s); MS m/e (MH)+ 410.

Workup

  1. customAll volatiles were removed in vacuo
  2. customthe residue triturated with Et2O (3 mL)
  3. filtrationthe solid filtered
  4. washwashed with Et2O (2×5 mL), isohexane (2×5 mL)

Sources & evidence

ORD record
ord-8f7e62546c3e4d0a90af142a33eae5f4
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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