Hydrochloride methanol → HCID 178480095, compound

HRID 575666Notes

Reaction equation

HRID 575666 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][C:17]=2[C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29](=[O:36])[N:28]([CH3:37])[CH:27]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Cl.CO>CO.C(Cl)Cl>[OH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:18][C:17]=2[C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29](=[O:36])[N:28]([CH3:37])[CH:27]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 21893726Hydrochloride methanolHCID 131732851HCID 131732851, compound

Product 1

HCID 178480095HCID 178480095, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound from step 1 (180.0 mg, 0.33 mmol) in dry MeOH (5 mL) and DCM (3 mL) was added dropwise HCl/MeOH (0.3 mL, 1.2 mmol, 4M) at 0° C. and then stirred at r.t. for 20 min. TLC showed the starting material was consumed completely. The mixture was concentrated and the residue was purified by prep-HPLC to afford the title compound (130.0 mg, 97.8%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.50 (d, J=7.6 Hz, 1H), 7.98 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 7.86 (d, J=2.4 Hz, 1H), 7.55 (t, J=6.8 Hz, 1H), 7.51 (t, J=6.8 Hz, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.11 (d, J=8.8 Hz, 1H), 7.05 (s, 1H), 4.42-4.35 (m, 1H), 3.67 (s, 3H), 3.65-3.62 (m, 1H), 3.10 (s, 3H), 2.01-1.89 (m, 2H), 1.71-1.65 (m, 2H), 1.36-1.34 (m, 4H). LCMS (M+H)+=428.1 (M+1)+

Workup

  1. customwas consumed completely
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-8a0a898a3b0c4b8c8f1c284fbabbfe76
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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