1-Methylazetidin-3-amine xhydrochloride → HCID 86693177, compound

HRID 575164Notes

Reaction equation

HRID 575164 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.[CH3:29][N:30]1[CH2:33][CH:32]([NH2:34])[CH2:31]1>>[F:17][C:15]1[C:14]([C:18]#[C:19][C:20]([OH:23])([CH3:21])[CH3:22])=[CH:13][C:12]2[C:6]3[N:7]([C:24]([C:25]([NH:34][CH:32]4[CH2:33][N:30]([CH3:29])[CH2:31]4)=[O:26])=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=3)[CH2:8][CH2:9][O:10][C:11]=2[CH:16]=1

Participants

3

Reactant 2

HCID 670505831-Methylazetidin-3-amine xhydrochlorideHCID 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 86693177HCID 86693177, 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 (0.06 g) was reacted with 1-methylazetidin-3-amine hydrochloride similar to as described in Example 2 to afford 13.4 mg of 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-N3-(1-methylazetidin-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide following reverse phase hplc purification. MS (Q1) 442 (M)+. 1H NMR (400 MHz, DMSO) δ 11.76 (d, J=6.7 Hz, 1H), 8.61 (d, J=8.4 Hz, 1H), 8.41 (s, 1H), 7.90 (s, 1H), 7.01 (d, J=10.5 Hz, 1H), 5.48 (s, 1H), 5.01-4.93 (m, 2H), 4.55-4.49 (m, 2H), 4.37 (dd, J=13.4, 6.7 Hz, 1H), 3.58 (t, J=7.2 Hz, 2H), 2.84 (t, J=7.1 Hz, 2H), 2.24 (s, 3H), 1.49 (s, 6H).

Sources & evidence

ORD record
ord-17a8dff4acd74b239364ab7a4cdde2f9
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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