Dimethylamine → HCID 22050474, compound

HRID 1832040Notes

Reaction equation

[Br:1][C:2]1[C:3](=[O:30])[N:4]([C:22]2[C:27](F)=[CH:26]C=CC=2F)[C:5]([CH2:18][N:19]([CH3:21])[CH3:20])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].C[NH:32][CH3:33].[CH2:34]1COC[CH2:35]1>>[Br:1][C:2]1[C:3](=[O:30])[N:4]([CH2:22][C:27]2[CH:26]=[N:32][CH:33]=[CH:34][CH:35]=2)[C:5]([CH2:18][N:19]([CH3:20])[CH3:21])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

Reactant 3

HCID 674Dimethylamine

HCID 8028Tetrahydrofuran

HCID 22050098HCID 22050098, compound

Product 1

HCID 22050474HCID 22050474, compound

Procedure

The title compound was prepared in a similar manner to the procedure outlined below for 3-bromo-4-[(2,4-difluorobenzyl)oxy]-1-(2,6-difluorophenyl)-6-[(dimethylamino) -methyl]pyridin-2(1H)-one using the aldehyde (300 mg, 0.85 mmol) described above and 2.0 N THF solution of dimethylamine (500 μL, 1 mmol) to give 110 mg (34%) of a colorless oil. The oil was then dissolved in MeOH (1 mL) and stirred with fumaric acid (25 mg) for 1 h. The resulting precipitate was filtered, washed with diethyl ether, and dried to give the pure product as it's fumurate salt. 1H-NMR (DMSOd6/400 MHz). δ 8.43-8.41 (m, 1H), 8.35 (s, 1H), 7.67-7.61 (m, 1H), 7.44-7.40 (m, 1H), 7.35-7.29 (m, 2H), 7.17-7.12 (m, 1H), 6.62 (s, 1H), 6.60 (s, 1H), 5.41 (s, 2H), 5.32 (s, 2H), 3.13 (s, 2H), 2.12 (s, 6H). LC/MS, tr=1.55 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 464 (M+H).

Sources & evidence

ORD record: ord-cd5f10d0082940f9ae63131cf4aa0dc7
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067540B2

Reaction notes

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