Sodium Azide → HCID 71255791, compound

HRID 540169Notes

Reaction equation

HRID 540169 reaction equation
[O:1]=[S:2]1(=[O:25])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH2:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:24])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.Br[CH:27]([CH3:31])[C:28](Cl)=[O:29].[N-:32]=[N+]=[N-].[Na+]>>[O:25]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][C:28](=[O:29])[C@H:27]([CH3:31])[NH2:32])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:24])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 33557Sodium AzideHCID 979802-Bromopropanoyl chlorideHCID 712554832-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine

Product 1

HCID 71255791HCID 71255791, compound

Procedure

The title compound was prepared in analogy to Example 40-2 in Scheme 18 by using 2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine, 2-bromopropionyl chloride and sodium azide. MS obsd. (ESI+) [(M+H)+] 425, 1H NMR (400 MHz, CD3OD) δ ppm 8.07-7.85 (m, 3 H), 7.64-7.51 (m, 2 H), 7.46-7.35 (m, 2 H), 5.22-5.08 (m, 2 H), 4.51-4.42 (m, 1 H), 3.65-3.53 (m, 2 H), 3.37 (s, 3 H), 2.51-2.40 (m, 3 H), 1.73 (d, J=7.07 Hz, 1 H), 1.30 (d, J=2.78 Hz, 2 H).

Sources & evidence

ORD record
ord-3de9ede325a542e29774f1bc142e33c1
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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