(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → HCID 86693541, compound

HRID 575474Notes

Reaction equation

HRID 575474 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH:18]4[CH2:20][CH2:19]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:21]=1.[CH3:22][C:23]1[O:27][N:26]=[C:25]([C@:28]([OH:32])([C:30]#[CH:31])[CH3:29])[CH:24]=1>>[CH:18]1([C:12]2[N:8]3[CH2:9][CH2:10][O:11][C:5]4[CH:4]=[CH:3][C:2]([C:31]#[C:30][C@@:28]([OH:32])([C:25]5[CH:24]=[C:23]([CH3:22])[O:27][N:26]=5)[CH3:29])=[CH:21][C:6]=4[C:7]3=[N:14][C:13]=2[C:15]([NH2:17])=[O:16])[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 86693542HCID 86693542, compound

Product 1

HCID 86693541HCID 86693541, compound

Procedure

Similar to as described in General Procedure G, 10-bromo-3-cyclopropyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with (R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol to give the titled compound. MS+419.2. 1H NMR (400 MHz, DMSO) δ 8.52 (d, J=2.2 Hz, 1H), 7.42 (br s, 1H), 7.31 (dd, J=8.5, 2.2 Hz, 1H), 7.02 (d, J=8.5 Hz, 1H), 6.95 (br s, 1H), 6.45 (s, 1H), 6.35 (s, 1H), 4.50 (m, 4H), 2.40 (s, 3H), 1.80 (s, 3H), 1.76 (m, 1H), 0.98 (m, 2H), 0.84 (m, 2H).

Sources & evidence

ORD record
ord-11d5a722a248454a8ddce44af324d874
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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