Hydrochloric Acid → HCID 6914613, compound

HRID 2307751Notes

Reaction equation

HRID 2307751 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:28]C(=O)OC(C)(C)C)[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:19]=2)=[CH:2]1.Cl>ClCCl.O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH2:28])[CH2:12][O:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18](/[CH:20]=[CH:21]/[C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[CH:19]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131724689HCID 131724689, compound

Product 1

HCID 6914613HCID 6914613, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 2B (603 mg, 1.28 mmol) in dichloromethane (20 mL) at room temperature was treated with 4N HCl in dioxane (5 mL), stirred for 2 hours, and concentrated. The residue was dissolved in water (1.5 mL) and freeze-dried to provide the desired product as the hydrochloride salt (610 mg, 99%). MS (DCI/NH3) m/e 371 (M+H)+, 1HNMR (CD3OD) δ 8.76 (d, J=6.8 Hz, 2H), 8.52 (d, J=1.4 Hz, 1H), 8.38 (d, J=2.4 Hz, 1H), 8.16 (d, J=7.1 Hz, 2H), 7.86 (d, J=16.6 Hz, 1H), 7.77 (m, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.52 (d, J=8.1 Hz, 1H), 7.50 (d, J=16.6 Hz, 1H), 7.39 (d, J=8.1 Hz, 1H), 7.28 (s, 1H), 7.13 (m, 1H), 7.03 (m, 1H), 4.39 (dd, J=3.4, 10.5 Hz, 1H), 4.25 (dd, J=5.4, 10.5 Hz, 1H), 4.00 (m, 1H), 3.30 (m, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in water (1.5 mL)
  3. customfreeze-dried

Sources & evidence

ORD record
ord-7e5f44eb1d404646b7c078cc53dd3071
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

Loading…