Hydrochloric Acid → HCID 66625565, compound

HRID 2367056Notes

Reaction equation

HRID 2367056 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[C:13]([CH2:15][C@H:16]2[C@@H:20]([O:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)[CH:12]=[C:11]([CH3:41])[CH:10]=1)=O)(C)(C)C.Cl>CO>[Cl:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][O:21][C@H:20]1[CH2:19][NH:18][CH2:17][C@H:16]1[CH2:15][C:13]1[N:14]=[C:9]([NH2:8])[CH:10]=[C:11]([CH3:41])[CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66625841HCID 66625841, compound

Product 1

HCID 66625565HCID 66625565, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 21b (70 mg, 0.10 mmol) in MeOH (2 mL) was added 6 N HCl (4 mL) at room temperature. The mixture was stirred for 12 h and then concentrated. The crude product was purified by recrystallization (EtOH/H2O) to give inhibitor 10 (38 mg, 97%): 1H NMR (500 MHz, CDCl3) δ 2.26 (s, 1H), 2.55-2.65 (m, 1H), 2.78-2.85 (dd, J=7.0, 15.0 Hz, 1H), 2.88-2.95 (dd, J=8.0, 15.0 Hz, 1H), 3.02-3.07 (dd, J=15.5, 16.0 Hz, 1H), 3.25-3.33 (m, 2H), 3.39-3.43 (m, 3H), 3.71-3.74 (t, J=6.5 Hz, 2H), 3.89-3.96 (t, J=15.0 Hz, 2H), 4.29 (s, 1H), 6.68 (s, 1H), 6.72 (s, 1H), 7.50-7.53 (dd, J=5.0, 7.5 Hz, 1H), 7.70-7.73 (d, J=8.0 Hz, 1H), 7.92-7.96 (ddd, J=2.0, 8.0, 8.0 Hz, 1H), 8.45-8.55 (d, J=5.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 21.3, 29.1, 37.8, 42.0, 46.4, 46.9, 50.4, 50.6, 50.8, 53.3, 69.4, 108.0, 114.8, 115.1, 116.7, 118.7, 120.9, 121.0, 126.9, 139.1, 147.4, 149.2, 149.4, 149.6, 149.8, 152.5, 159.3; LC-TOF (M+H+) calcd for C20H28F2N5O 392.2262, found 392.2265.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by recrystallization (EtOH/H2O)

Sources & evidence

ORD record
ord-9188ff487a5e413888f675a4c2c5f7e6
Source dataset
uspto-grants-2014_04
Patent number
US08697879B2

Reaction notes

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