Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetate → (S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-hydroxyacetate

HRID 1481997Notes

Reaction equation

HRID 1481997 reaction equation
[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=4)[N:19]=[C:15]3[CH:14]=[C:13]([CH3:27])[C:12]=2[C:28](=[O:33])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].C(C1(C)CCN(C2N3C=C(C(OCC)=O)N=C3C=C(C)C=2[C@H](O)C(OC)=O)CC1)CC=C>>[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=4)[N:19]=[C:15]3[CH:14]=[C:13]([CH3:27])[C:12]=2[C@H:28]([OH:33])[C:29]([O:31][CH3:32])=[O:30])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 118308795Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetateHCID 118319909(S)-ethyl 5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-hydroxy-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 118308883(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-hydroxyacetateYield 80%

Procedure

Prepared from methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-oxoacetate in 80% yield following the same procedure as (S)-ethyl 5-(4-(but-3-en-1-yl)-4-methylpiperidin-1-yl)-6-(1-hydroxy-2-methoxy-2-oxoethyl)-7-methylimidazo[1,2-a]pyridine-2-carboxylate. 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 8.01 (s, 1H), 7.96 (br. s., 1H), 7.51-7.31 (m, 3H), 6.24-6.09 (m, 1H), 5.58-5.50 (m, 2H), 5.46-5.40 (m, 1H), 4.83-4.72 (m, 1H), 4.02 (d, J=5.0 Hz, 2H), 3.90 (t, J=11.8 Hz, 2H), 3.79 (s, 3H), 2.91 (d, J=8.0 Hz, 1H), 2.66 (d, J=10.8 Hz, 1H), 2.49 (s, 3H), 1.99 (t, J=11.8 Hz, 2H), 1.82 (qd, J=12.9, 4.8 Hz, 2H), 1.34 (s, 3H); LCMS (ESI, M+1): 528.25.

Sources & evidence

ORD record
ord-90bca0fa1ed845d08edf3b3e2dd56286
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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