Aminoacetonitrile hydrochloride → HCID 86693176, compound

HRID 575161Notes

Reaction equation

[C:1]([C:4]1[N:5]=[C:6]2[C:12]3[CH:13]=[C:14]([C:18]#[C:19][C:20]([OH:23])([CH3:22])[CH3:21])[C:15]([F:17])=[CH:16][C:11]=3[O:10][CH2:9][CH2:8][N:7]2[C:24]=1[C:25](O)=[O:26])(=[O:3])[NH2:2].Cl.[NH2:29][CH2:30][C:31]#[N:32]>>[C:30]([CH2:31][NH:32][C:25]([C:24]1[N:7]2[CH2:8][CH2:9][O:10][C:11]3[CH:16]=[C:15]([F:17])[C:14]([C:18]#[C:19][C:20]([OH:23])([CH3:22])[CH3:21])=[CH:13][C:12]=3[C:6]2=[N:5][C:4]=1[C:1]([NH2:2])=[O:3])=[O:26])#[N:29]

Participants

Reactant 2

HCID 11491918Aminoacetonitrile hydrochloride

HCID 866931712-Carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylic acid

Product 1

HCID 86693176HCID 86693176, compound

Procedure

2-Carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylic acid (0.05 g) was reacted with aminoacetonitrile hydrochloride similar to as described in Example 2 to afford 9 mg of N3-(cyanomethyl)-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide following reverse phase hplc purification. MS (Q1) 412 (M)+. 1H NMR (400 MHz, DMSO) δ 12.03 (t, J=5.3 Hz, 1H), 8.65 (d, J=8.4 Hz, 1H), 8.53 (s, 1H), 8.04 (s, 1H), 7.03 (d, J=10.5 Hz, 1H), 5.47 (s, 1H), 5.07-4.90 (m, 2H), 4.66-4.53 (m, 2H), 4.39 (d, J=5.3 Hz, 2H), 1.50 (s, 6H).

Sources & evidence

ORD record: ord-53a927ce9a4b446b86b678a36c77d6aa
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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