Hydrochloric Acid → HCID 59843324, compound

HRID 2196581Notes

Reaction equation

HRID 2196581 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][N:26](C)[C:27](=O)OC(C)(C)C)[CH2:20][CH2:19]3)=[CH:13][N:12]2[CH:35]=1.Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH:18]3[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][NH:26][CH3:27])[CH2:20][CH2:19]3)=[CH:13][N:12]2[CH:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59843328HCID 59843328, compound

Product 1

HCID 59843324HCID 59843324, compoundYield 127.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 223 (45 mg, 0.094 mmol) was stirred in a saturated solution of HCl in DCM (1 mL) for 1.5 hours. The reaction was taken to dryness under high vacuum to give 224 (45.5 mg, tris-HCl salt) as a white solid. 1H NMR: (DMSO-d6) δ(ppm): 11.23 (br s, 1H), 9.51 (br s, 2H), 8.74 (s, 1H), 8.69 (s, 1H), 8.22 (d, J=8.0 Hz, 1H), 7.71 (s, 1H), 7.52 (dt, J=1.6, 8.8 Hz, 1H), 7.27 (d, J=7.6 Hz, 1H), 7.17 (t, J=7.2 Hz, 1H), 3.98 (s, 3H), 3.75-3.72 (m, 2H), 3.54 (m, 4H), 3.24-3.16 (m, 2H), 3.05-2.99 (m, 1H), 2.69 (s, 3H), 2.60 (t, J=5.2 Hz, 3H), 2.19-2.05 (m, 4H). LRMS (ESI): (calc.) 378.2 (found) 379.4 (MH)+.

Sources & evidence

ORD record
ord-e408a80203fc489e90e7ac40341decb3
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

Loading…