Hydrochloric Acid → HCID 67174721, compound

HRID 1816019Notes

Reaction equation

[Li+].[OH-].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C@@H:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[CH2:32][CH2:31][CH2:30][NH:29][C:28]=4[N:27]=3)=[CH:19][CH:18]=2)[CH2:10][C:11]([O:13]CC)=[O:12])[CH:4]=1.Cl>C1COCC1.O>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C@@H:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][C:26]3[CH:35]=[CH:34][C:33]4[CH2:32][CH2:31][CH2:30][NH:29][C:28]=4[N:27]=3)=[CH:19][CH:18]=2)[CH2:10][C:11]([OH:13])=[O:12])[CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1.0 M LiOH (2.6 mL, 2.6 mmole) was added to a solution of ethyl (S)-3-(pyridin-3-yl)-4-[4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl]butanoate (572 mg, 1.28 mmole) in THF/H2O (8 mL), and the mixture was heated at 50° C. After 18 hr, the reaction was cooled to RT and acidified to pH 6.0 with 10% HCl. The precipitated solid was collected by suction filtration, washed with H2O, and dried in vacuo to afford the title compound (414 mg, 77%): 1H NMR (400 MHz, MeOH-d4) δ 8.28 (dd, J=4.9, 1.4 Hz, 1 H), 8.21 (d, J=1.8 Hz, 1 H). 7.68 (d, J=8.0 Hz, 1 H), 7.25-7.27 (m, 2 H), 6.91 (d, I=8.6 Hz, 2 H), 6.71 (d, J=8.6 Hz, 2 H), 6.53 (d, J=7.3 Hz, 1 H), 4.08-4.22 (m, 2 H), 3.30-3.45 (m, 3 H), 2.90-3.05 (m, 3 H), 2.70-2.85 (m, 3 H), 2.68 (dd, J=15.2, 6.7 Hz, 1 H), 2.58 (dd, J=15.2, 8.5 Hz, 1 H), 1.80-1.97 (m, 2 H); MS (ES) m/e 418 (M+H)+. Anal. Calcd for C23H25N3O3.0.25H2O: C, 71.15; H, 6.57; N, 9.96. Found: C, 71.11; H, 6.66; N, 9.82.

Workup

temperaturethe reaction was cooled to RT
filtrationThe precipitated solid was collected by suction filtration
washwashed with H2O
customdried in vacuo

Sources & evidence

ORD record: ord-f559161c0015458c91b9b1b2c00e6633
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881736B1

Reaction notes

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