Dimethylformamide → [7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-furo[3,2-c]pyridin-6-yl]-methylamine

HRID 911960Notes

Reaction equation

HRID 911960 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:13]1[C:14]2[O:22][CH:21]=[C:20]([C:23]3CCNCC=3)[C:15]=2[CH:16]=[N:17][C:18]=1N)[CH3:11].CI.C[CH2:32][N:33]([CH:37]([CH3:39])C)[CH:34]([CH3:36])C.[CH3:40][N:41](C=O)C>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:13]1[C:14]2[O:22][CH:21]=[C:20]([C:23]3[CH2:39][CH2:37][N:33]([CH3:32])[CH2:34][CH:36]=3)[C:15]=2[CH:16]=[N:17][C:18]=1[NH:41][CH3:40])[CH3:11]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 578124807-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine

Product 1

HCID 57812648[7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-furo[3,2-c]pyridin-6-yl]-methylamine

Procedure

A mixture of 7-[(R)-1-(2,6-dichloro-3-fluorophenyl)-ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)-furo[3,2-c]pyridin-6-ylamine (10.0 mg, 0.0237 mmol), methyl iodide (6.72 mg, 0.0474 mmol), DIPEA (0.02 mL, 0.1 mmol), and DMF (0.5 mL) was stirred at rt for 20 min. The solution was used directly for HPLC purification. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a brown solid. 1H NMR (CDCl3, 400 MHz): δ=1.88 (d, J=6.6 Hz, 3H), 2.90 (d, J=6.3 Hz, 2H), 3.50 (br, s, 6H), 3.99 (br, s, 2H), 4.31 (br, s, 2H), 4.87 (br, s, 1H), 6.17 (br, s, 1H), 6.51 (d, J=6.8 Hz, 1H), 7.06 (t, J=8.5 Hz, 1H), 7.28-7.34 (m, 1H), 7.51 (s, 1H), 8.19 (br, s, 1H). MS (ES+): m/z 450.05 [MH+]. HPLC: tR=2.55 min (ZQ3, polar—5 min).

Workup

  1. customThe solution was used directly for HPLC purification
  2. additionThe fractions containing the pure product
  3. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-157efb0f245a4898ac05bb1162e58d46
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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