Hydrochloric Acid → HCID 178490677, compound

HRID 2196823Notes

Reaction equation

HRID 2196823 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 m 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, 3 H) 1.40 (s, 9 H) 3.64-3.73 (m, 1 H) 3.86 (s, 3 H) 4.26-4.31 (m, 2 H) 7.09 (d, J=8.82 Hz, 1 H) 7.18 (s, 1 H) 7.41 (dd, J=8.82, 2.71 Hz, 1 H) 7.74 (d, J=2.71 Hz, 1 H); 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 m particle size)

Sources & evidence

ORD record
ord-2fca4a4236a449979a57c67f9030a182
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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