(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → (R)-3-cyclopropyl-9-fluoro-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

HRID 575473Notes

Reaction equation

HRID 575473 reaction equation
Br[C:2]1[C:3]([F:23])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:19]4[CH2:21][CH2:20]4)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:22]=1.[CH3:24][C:25]1[O:29][N:28]=[C:27]([C@:30]([OH:34])([C:32]#[CH:33])[CH3:31])[CH:26]=1>>[CH:19]1([C:13]2[N:8]3[CH:9]4[CH2:10][CH:11]([C:5]5[CH:4]=[C:3]([F:23])[C:2]([C:33]#[C:32][C@@:30]([OH:34])([C:27]6[CH:26]=[C:25]([CH3:24])[O:29][N:28]=6)[CH3:31])=[CH:22][C:6]=5[C:7]3=[N:15][C:14]=2[C:16]([NH2:18])=[O:17])[CH2:12]4)[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 8669353710-bromo-3-cyclopropyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Product 1

HCID 86693540(R)-3-cyclopropyl-9-fluoro-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Procedure

Similar to as described in General Procedure E, 10-bromo-3-cyclopropyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with (R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol to give the titled compound. MS+447.2. 1H NMR (400 MHz, DMSO) δ 8.68 (d, J=7.5 Hz, 1H), 7.45 (br s, 1H), 7.26 (d, J=10.1 Hz, 1H), 6.92 (br s, 1H), 6.57 (s, 1H), 6.35 (s, 1H), 5.26 (m, 1H), 3.68 (m, 1H), 314 (m, 1H), 2.41 (s, 3H), 1.82 (s, 3H), 1.77-1.61 (overlapping m, 3H), 0.99 (m, 1H), 0.68 (m, 1H).

Sources & evidence

ORD record
ord-b2ca8af19be64b0ba451826a21771ce8
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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