Ammonia methanol dichloromethane → HCID 86694629, compound

HRID 63330Notes

Reaction equation

HRID 63330 reaction equation
[CH:1]1([O:7][C:8]2[N:13]=[C:12]([C@H:14]([OH:18])[CH2:15][C:16]#[N:17])[CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N.CO.C(Cl)Cl>>[NH2:17][CH2:16][CH2:15][C@H:14]([C:12]1[CH:11]=[CH:10][CH:9]=[C:8]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:13]=1)[OH:18]

Participants

3

Reactant 2

HCID 21584172Ammonia methanol dichloromethaneHCID 86694630HCID 86694630, compound

Product 1

HCID 86694629HCID 86694629, compound

Procedure

Reduction of (R)-3-(6-(cyclohexyloxy)pyridin-2-yl)-3-hydroxypropanenitrile following the method described in Example 6 gave after flash chromatography purification (15%-25% 7N NH3/MeOH—CH2Cl2 gradient) Example 26 as a colorless oil. Yield (0.4 g, 33%); 1H NMR (400 MHz, CD3OD) δ 7.61 (t, J=7.8 Hz, 1H), 7.00 (d, J=7.6 Hz, 1H), 6.58 (d, J=8.4 Hz, 1H), 5.05-4.96 (m, 1H), 4.40-4.28 (m, 1H), 2.84 (t, J=6.8 Hz, 2H), 2.08-1.74 (m, 6H), 1.62-1.32 (m, 6H); RP-HPLC tR=7.04 min; ESI-MS m/z 251.2 [M+H]+.

Workup

  1. customgave
  2. customYield (0.4 g, 33%)

Sources & evidence

ORD record
ord-28d6ce669149475a8583161beccef353
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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