Ammonia methanol dichloromethane → HCID 86694625, compound

HRID 63328Notes

Reaction equation

HRID 63328 reaction equation
[CH:1]1([CH2:7][S:8][C:9]2[N:14]=[C:13]([C@H:15]([OH:19])[CH2:16][C:17]#[N:18])[CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N.CO.C(Cl)Cl>>[NH2:18][CH2:17][CH2:16][C@H:15]([C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([S:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:14]=1)[OH:19]

Participants

3

Reactant 2

HCID 21584172Ammonia methanol dichloromethaneHCID 86694626HCID 86694626, compound

Product 1

HCID 86694625HCID 86694625, compound

Procedure

Reduction of (R)-3-(6-((cyclohexylmethyl)thio)pyridin-2-yl)-3-hydroxypropanenitrile following the method described in Example 6 gave after flash chromatography purification (15%-20% 7N NH3/MeOH—CH2Cl2 gradient) Example 25 as a colorless oil. Yield (0.3 g, 43%); 1H NMR (400 MHz, CD3OD) δ 7.56 (t, J=7.6 Hz, 1H), 7.17 (d, J=7.6 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 4.75-4.72 (m, 1H), 3.04 (d, J=7.2 Hz, 2H), 2.80 (t, J=7.6 Hz, 2H), 2.03-1.98 (m, 1H), 1.94-1.54 (m, 7H), 1.30-0.99 (m, 5H); RP-HPLC tR=9.63 min; ESI-MS m/z 281.2 [M+H]+.

Workup

  1. customgave
  2. customYield (0.3 g, 43%)

Sources & evidence

ORD record
ord-5b1a15eb128e4b27b5d6b47934dff833
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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