Diisopropylethylamine → HCID 68973519, compound

HRID 1782585Notes

Reaction equation

HRID 1782585 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:3])[CH3:2].Br[CH2:29][C:30]1[N:35]=[C:34]([C:36]#[N:37])[CH:33]=[CH:32][CH:31]=1.CCN(C(C)C)C(C)C>CC#N>[C:1]([O:5][C:6](=[O:27])[NH:7][CH2:8][CH2:9][C@H:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[C:34]([C:36]#[N:37])[N:35]=2)[C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:14][CH2:13]1)[CH3:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 272816606-(Bromomethyl)pyridine-2-carbonitrileHCID 68971155(R)-{3-[4-(4-methoxy-phenylamino)-piperidin-1-yl]-butyl}-carbamic acid tert-butyl ester

Product 1

HCID 68973519HCID 68973519, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using General Procedure E, (R)-{3-[4-(4-methoxy-phenylamino)-piperidin-1-yl]-butyl}-carbamic acid tert-butyl ester (0.681 g, 1.81 mmol), 6-bromomethyl-pyridine-2-carbonitrile (0.535 g, 2.71 mmol) and DIPEA (630 μL, 3.62 mmol) in CH3CN (20 mL) at 55° C. for 16 h gave the crude product as a pale brown oil. Purification by column chromatography on silica gel (CH2Cl2:MeOH:, 95:5, v/v) afforded (R)-(3-{4-[(6-cyano-pyridin-2-ylmethyl)-(4-methoxy-phenyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.696 g, 78%) as a yellow crystalline solid. 1H NMR (CDCl3) δ 0.95 (d, 3H, J=6.0 Hz), 1.40 (s+m, 11H), 1.65 (m, 4H), 1.86 (m, 2H), 2.13 (br t, 1H), 2.54 (br t, 1H), 2.73-2.86 (m, 3H), 3.06 (m, 1H), 3.31 (m, 1H), 3.54 (m, 1H), 3.73 (s, 3H), 4.50 (s, 2H), 6.06 (br s, 1H), 6.68 (d, 2H, J=9.0 Hz), 6.76 (d, 2H, J=9.0 Hz), 7.52 (d, 1H, J=6.0 Hz), 7.54 (d, 1H, J=6.0 Hz), 7.70 (t, 1H, J=6.0 Hz).

Workup

  1. customat 55° C.
  2. customfor 16 h
  3. customgave the crude product as a pale brown oil
  4. customPurification by column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record
ord-164f1aed3a24455c921e368e084b7b1e
Source dataset
uspto-grants-2009_03
Patent number
US07498346B2

Reaction notes

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