Hydrochloric Acid → HCID 67441794, compound

HRID 1400810Notes

Reaction equation

HRID 1400810 reaction equation
[P:1]([O:13][CH2:14][C:15]([N:17]([CH2:22][C:23]1[CH:24]=[N:25][C:26]([C:29]2[S:37][C:36]3[C:31](=[N:32][CH:33]=[CH:34][C:35]=3[O:38][C:39]3[CH:44]=[CH:43][C:42]([NH:45][C:46]([NH:48][CH:49]4[CH2:51][CH2:50]4)=[O:47])=[CH:41][C:40]=3[F:52])[CH:30]=2)=[CH:27][CH:28]=1)[CH2:18][CH2:19][O:20][CH3:21])=[O:16])([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].Cl.O1CCOCC1>C(Cl)Cl>[P:1]([OH:8])([OH:3])([O:13][CH2:14][C:15]([N:17]([CH2:22][C:23]1[CH:24]=[N:25][C:26]([C:29]2[S:37][C:36]3[C:31](=[N:32][CH:33]=[CH:34][C:35]=3[O:38][C:39]3[CH:44]=[CH:43][C:42]([NH:45][C:46]([NH:48][CH:49]4[CH2:51][CH2:50]4)=[O:47])=[CH:41][C:40]=3[F:52])[CH:30]=2)=[CH:27][CH:28]=1)[CH2:18][CH2:19][O:20][CH3:21])=[O:16])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68224083HCID 68224083, compound

Product 1

HCID 67441794HCID 67441794, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 33 from the previous step in DCM (15 mL) was added a solution of 4M HCl in 1,4-dioxane (0.44 mL, 1.75 mmol). The reaction mixture (suspension) was stirred at RT for 1 h. The solid was collected by filtration, rinsed with DCM and dried under high vacuum. The residue was suspended in MeOH, concentrated and triturated with a minimum of methanol/water to afford the title compound 34 (136 mg, 0.21 mmol, 60% over 3 steps) as an off-white fluffy solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): mixture of rotamers, 8.71 (s, 1H), 8.58-8.48 (m, 2H), 8.37 and 8.33 (2 s, 1H), 8.29 and 8.24 (2d, J=8.2 Hz, 1H), 7.86-7.77 (m, 1H), 7.73 (dd, J=13.6, 2.4 Hz, 1H), 7.38 (t, J=9.1 Hz, 1H), 7.20 (bd, J=9.0 Hz, 1H), 6.64 (d, J=5.3 Hz, 1H), 6.57 (d, J=2.5 Hz, 1H), 4.74-4.50 (m, 4H), 3.47 (bs, 4H), 3.24 and 3.21 (2s, 3H), 2.59-2.51 (m, 1H), 0.73-0.58 (m, 2H), 0.50-0.36 (m, 2H). MS (m/z): 646.7 (M+H).

Workup

  1. filtrationThe solid was collected by filtration
  2. washrinsed with DCM
  3. customdried under high vacuum
  4. concentrationconcentrated
  5. customtriturated with a minimum of methanol/water

Sources & evidence

ORD record
ord-519b141a9d25486b823a0ef2313c5bb5
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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