Ammonia → (4s)-4-N-(5-Bromopyridin-3-yl)-1-azatricyclo[3.3.1.13,7]decan-4-amine

HRID 878436Notes

Reaction equation

HRID 878436 reaction equation
[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([C:4]3=O)[CH2:2]1)[CH2:8]2.[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=1.N>>[Br:19][C:17]1[CH:18]=[C:13]([NH:12][C@@H:4]2[CH:5]3[CH2:10][N:1]4[CH2:8][CH:7]([CH2:9][CH:3]2[CH2:2]4)[CH2:6]3)[CH:14]=[N:15][CH:16]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-oneHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 24987501(4s)-4-N-(5-Bromopyridin-3-yl)-1-azatricyclo[3.3.1.13,7]decan-4-amine

Procedure

Prepared from 1-azatricyclo[3.3.1.13,7]decan-4-one (1.51 g, 10 mmol; see Becker, D. P.; Flynn, D. L. Synthesis 1992, 1080) and 3-amino-5-bromopyridine (2.06 g, 12 mmol; Aldrich) according to the procedure described in Example 65A: 1H NMR (300 MHz, methanol-D4) δ ppm 1.81-1.99 (m, 2H), 2.02-2.15 (m, 1H), 2.17-2.40 (m, 4H), 3.44-3.51 (m, 2H), 3.53-3.66 (m, 4H), 3.91 (s, 1H), 7.26-7.41 (m, 1H), 7.84 (d, J=1.7 Hz, 1H), 8.01 (d, J=2.7 Hz, 1H). MS (DCI/NH3) m/z=308/310 (M+H)+.

Sources & evidence

ORD record
ord-ac9a3ef4cec547539773cd82743448d6
Source dataset
uspto-grants-2015_03
Patent number
US08987453B2

Reaction notes

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