1,2-Dichloroethane → HCID 22649349, compound

HRID 393267Notes

Reaction equation

[CH2:1]([O:5][C:6]1[C:7]([O:19][CH3:20])=[CH:8][CH:9]=[C:10]2[C:15]=1[NH:14][C:13](=[O:16])[C:12]([CH2:17][NH2:18])=[CH:11]2)[CH2:2][CH2:3][CH3:4].[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](O)=[O:30])=[CH:24][CH:23]=1.ON1C2C=CC=CC=2N=N1.C(Cl)CCl.C(=O)(O)[O-].[Na+]>CN(C=O)C.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:1]([O:5][C:6]1[C:7]([O:19][CH3:20])=[CH:8][CH:9]=[C:10]2[C:15]=1[NH:14][C:13](=[O:16])[C:12]([CH2:17][NH:18][C:29](=[O:30])[CH2:28][C:25]1[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=1)=[CH:11]2)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

8-Butoxy-3-aminomethyl-7-methoxy-2-oxo-1,2-dihydroquinoline (77.7 mg, 0.281 mmol) obtained in Example 7-2, 4-hydroxyphenylacetic acid (47.0 mg, 0.309 mmol) and N-hydroxybenzotriazole (41.8 mg, 0.309 mmol) were dissolved in DMF (3 ml), and EDC (59.2 mg, 0.309 mmol) and triethylamine (30 μl) were successively added thereto. The mixture was stirred at 50° C. for 3 hours, and then a saturated aqueous solution of sodium bicarbonate (3 ml) and toluene (5 ml) were added thereto. The precipitated crystals were collected through filtration, and washed successively with water, 1 N hydrochloric acid, water, and ethyl acetate to give the title compound (88 mg, yield 76%) as colorless crystals (Table 32).

Workup

filtrationThe precipitated crystals were collected through filtration
washwashed successively with water, 1 N hydrochloric acid, water, and ethyl acetate

Sources & evidence

ORD record: ord-3fc42c643cf24ea58615c27f6199ea0c
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806276B2

Reaction notes

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