Ethanol → HCID 67227293, compound

HRID 1848870Notes

Reaction equation

HRID 1848870 reaction equation
Cl[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[CH:40]=[C:39]([N:41]4[CH2:46][CH2:45][N:44]([CH2:47][C:48]5[CH2:53][CH2:52][C:51]([CH3:55])([CH3:54])[CH2:50][C:49]=5[C:56]5[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][CH:57]=5)[CH2:43][CH2:42]4)[CH:38]=[CH:37][C:13]=3[C:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][CH2:27][CH:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[C:22]([N+:34]([O-:36])=[O:35])[CH:21]=3)(=[O:19])=[O:18])=[O:15])[CH:9]=2)[NH:4][CH:3]=1.C([OH:65])C>Cl>[Cl:62][C:59]1[CH:58]=[CH:57][C:56]([C:49]2[CH2:50][C:51]([CH3:55])([CH3:54])[CH2:52][CH2:53][C:48]=2[CH2:47][N:44]2[CH2:45][CH2:46][N:41]([C:39]3[CH:38]=[CH:37][C:13]([C:14]([NH:16][S:17]([C:20]4[CH:25]=[CH:24][C:23]([NH:26][CH2:27][CH:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)=[C:22]([N+:34]([O-:36])=[O:35])[CH:21]=4)(=[O:18])=[O:19])=[O:15])=[C:12]([O:11][C:8]4[CH:9]=[C:10]5[C:5](=[CH:6][CH:7]=4)[NH:4][C:3](=[O:65])[CH2:2]5)[CH:40]=3)[CH2:42][CH2:43]2)=[CH:61][CH:60]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 87315881HCID 87315881, compound

Product 1

HCID 67227293HCID 67227293, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of EXAMPLE 265E (38 mg) in ethanol (5 mL) and 1 N aqueous HCl (5 mL) was stirred at 85° C. for 7 hours. The mixture was cooled to ambient temperature and concentrated. The residue was purified on reverse-phase HPLC on a C18 column using a water-acetonitrile gradient with ammonium acetate buffer to give the title compound. 1H NMR (500 MHz, dimethylsulfoxide-d6) δ 11.30 (br s, 1H), 10.33 (s, 1H), 8.61 (t, 1H), 8.54 (d, 1H), 7.84 (dd, 1H), 7.47 (d, 1H), 7.35 (d, 2H), 7.18 (d, 1H), 7.06 (d, 2H), 6.84 (s, 1H), 6.80 (d, 1H), 6.74 (d, 1H), 6.67 (dd, 1H), 6.20 (d, 1H), 3.85 (dd, 2H), 3.43 (s, 2H), 3.27 (t, 2H), 3.10 (br.s, 4H), 2.77 (br.s, 2H), 2.25-2.10 (m, 6H), 1.97 (br.s, 2H), 1.90 (m, 1H), 1.62 (dd, 2H), 1.40 (t, 2H), 1.27 (m, 2H), 0.94 (s, 6H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on reverse-phase HPLC on a C18 column

Sources & evidence

ORD record
ord-3e42b7ed981f4634ae958de4bfd76145
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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