5-(aminomethyl)furan-2-carbonitrile → HCID 68616560, compound

HRID 1887362Notes

Reaction equation

HRID 1887362 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][N:21]([C:24]2[S:25][C:26]([C:30](O)=[O:31])=[C:27]([CH3:29])[N:28]=2)[C:20](=[O:33])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][N:21]([C:24]2[S:25][C:26]([C:30]([NH:9][CH2:8][C:6]3[O:7][C:3]([C:2]#[N:1])=[CH:4][CH:5]=3)=[O:31])=[C:27]([CH3:29])[N:28]=2)[C:20](=[O:33])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 110838825-(aminomethyl)furan-2-carbonitrileHCID 249859522-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-methylthiazole-5-carboxylic acid

Product 1

HCID 68616560HCID 68616560, compoundYield 72%

Procedure

Following the procedure as described in Example 22, making variation only as required to use 5-(aminomethyl)furan-2-carbonitrile in place of benzo[b]thiophen-2-ylmethanamine to react with 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 72% yield: 1H NMR (300 MHz, DMSO-d6) δ 8.84 (t, J=5.6 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 7.52 (d, J=3.6 Hz, 1H), 7.45-7.30 (m, 5H), 6.55 (d, J=3.6 Hz, 1H), 6.39 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.6 Hz, 1H), 5.16 (s, 2H), 4.44 (d, J=5.6 Hz, 2H), 2.54 (s, 3H); MS (ES+) m/z 447.1 (M+1).

Sources & evidence

ORD record
ord-d65719b292ac455e8addf92f7ca4c18f
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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