Hydrochloric Acid → HCID 9841880, compound

HRID 1780357Notes

Reaction equation

HRID 1780357 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3C(OC(C)(C)C)=O)[CH:10]=[N:11][C:12]=2[Cl:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)C>[C:1]1([C:7]2[CH:8]=[C:9]([O:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][NH:17]3)[CH:10]=[N:11][C:12]=2[Cl:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22872688HCID 22872688, compound

Product 1

HCID 9841880HCID 9841880, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound from step 84a was deprotected and converted to the salt by treatment with HCl in ethanol to give the title compound (189 mg, 83% yield). mp 75°-80° C. MS (DCI/NH3) m/z 289 (M+H)+. 1 H NMR (D2O, 300 MHz) δ: 1.27-2.10 (m, 1H), 2.03-2.18 (m, 2H), 2.22-2.31 (m, 1H), 3.41 (t, J=7.5 Hz, 2H), 4.13 (m, 1H), 4.26 (m, 1H), 4.46 (dd, J=3.4, 10.8 Hz, 1H), 7.54 (m, 6H), 8.12 (d, J=3.0 Hz, 1H). Anal. Calcd for C16H17N2OCl·1.6 HCl: C, 55.53; H, 5.25; N, 7.96. Found: C, 55.53; H, 5.40; N, 8.07. [α]25D =+9.88° (c 0.27, MeOH).

Sources & evidence

ORD record
ord-b5dc956fbd4c4e8b9f43b5b929490cfd
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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