Hydrochloric Acid → HCID 178490677, compound

HRID 556708Notes

Reaction equation

HRID 556708 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:22][C@H:23]([NH:25]C(=O)OC(C)(C)C)[CH3:24])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CO.O1CCOCC1>[NH2:25][C@H:23]([CH3:24])[CH2:22][N:7]1[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[S:9]/[C:8]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178490678HCID 178490678, compound

Product 1

HCID 178490677HCID 178490677, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

In a 20 mL vial, to a solution of Example 59B (75 mg, 0.156 mmol) in MeOH (1 mL) was added a solution of hydrogen chloride (0.039 mL, 0.156 mmol) in dioxane and the mixture was stirred for 24 hr. The reaction was concentrated and the residue was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10-100% acetonitrile (A) and 10 mM ammonium acetate in water (B), at a flow rate of 2.0 mL/min (0-0.1 min 10% A, 0.1-2.6 min 10-100% A, 2.6-2.9 min 100% A, 2.9-3.0 min 100-10% A. 0.5 min post-run delay) to obtain the title compound (32 mg, 59%). 1H NMR (300 MHz, METHANOL-d4) δ ppm 1.26 (d, J=6.78 Hz, 3H) 1.40 (s, 9H) 3.64-3.73 (m, 1H) 3.86 (s, 3H) 4.26-4.31 (m, 2H) 7.09 (d, J=8.82 Hz, 1H) 7.18 (s, 1H) 7.41 (dd, J=8.82, 2.71 Hz, 1H) 7.74 (d, J=2.71 Hz, 1H); MS (DCI) m/z 382 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)

Sources & evidence

ORD record
ord-ea988a183aff4d60a58a6ef7151c3670
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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