Hydrochloric Acid → HCID 56835761, compound

HRID 1424645Notes

Reaction equation

HRID 1424645 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][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)[CH:12]=[C:11]([CH3:40])[CH:10]=1)=O)(C)(C)C.Cl>CO>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[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]([CH3:40])[CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86664069HCID 86664069, compound

Product 1

HCID 56835761HCID 56835761, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7a (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 3a (38 mg, 97%): 1H NMR (500 MHz, D2O) δ 2.18 (s, 3H), 2.68-2.73 (m, 1H), 2.76-2.82 (dd, J=7.0, 15.5 Hz, 1H), 2.85-2.90 (dd, J=8.0, 15.0 Hz, 1H), 3.04-3.09 (t, J=11.5 Hz, 1H), 3.15-3.25 (m, 2H), 3.39-3.43 (dd, J=8.5, 11.5 Hz, 1H), 3.50-3.53 (d, J=13.5 Hz, 1H), 3.53-3.60 (m, 1H), 3.73-3.80 (m, 1H), 4.05-4.10 (m, 1H), 4.22 (s, 2H), 6.47 (s, 1H), 6.53 (s, 1H), 7.12-7.14 (dd, J=1.0, 8.5 Hz, 1H), 7.16-7.18 (dd, J=1.0, 8.0 Hz, 1H), 7.35-7.40 (m, 1H); 13C NMR (125 MHz, D2O) δ 21.0, 28.8, 41.3, 44.67, 44.70, 46.4, 47.1, 49.3, 63.9, 78.0, 110.3, 114.0, 115.8, 115.9, 117.4, 117.5, 125.0, 125.1, 132.1, 132.2, 132.3, 132.4, 145.7, 153.8, 158.1, 160.1, 162.0; LC-TOF (M+H) calcd for C20H28FN4O 359.2247. found 359.2253.

Workup

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

Sources & evidence

ORD record
ord-5da26fe0bf1d4f2e935207f1f0cf58dd
Source dataset
uspto-grants-2015_01
Patent number
US08927730B2

Reaction notes

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