6-Bromopyridine-2-carboxylic acid → 3-Amino-1-(4-(cyclohexylmethoxy)pyridin-2-yl)propan-1-ol

HRID 63309

반응식

HRID 63309 반응식
[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15](=[O:19])[CH2:16][C:17]#[N:18])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.CSC.N.CO.C(Cl)Cl.BrC1N=C(C(O)=O)C=CC=1>>[NH2:18][CH2:17][CH2:16][CH:15]([C:11]1[CH:10]=[C:9]([O:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:14]=[CH:13][N:12]=1)[OH:19]

참가 물질

5

반응물 4

HCID 5939196-Bromopyridine-2-carboxylic acidHCID 12423031(Dimethyl sulfide)trihydroboronHCID 21584172Ammonia methanol dichloromethaneHCID 866945973-(4-(Cyclohexylmethoxy)pyridin-2-yl)-3-oxopropanenitrile

생성물 1

HCID 866945963-Amino-1-(4-(cyclohexylmethoxy)pyridin-2-yl)propan-1-ol

실험 절차

Reduction of 3-(4-(cyclohexylmethoxy)pyridin-2-yl)-3-oxopropanenitrile with borane-dimethylsulfide following the method used in Example 2 gave after flash chromatography purification (20%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 12 as a yellow oil. Yield (0.13 g, 43%); 1H NMR (400 MHz, DMSO-d6) δ 8.22 (d, J=4.5 Hz, 1H), 6.98 (d, J=2.3 Hz, 1H), 6.76 (dd, J=5.9, 2.8 Hz, 1H), 4.62-4.58 (m, 1H), 3.94 (d, J=5.8 Hz, 2H), 2.72-2.58 (m, 2H), 1.88-1.58 (m, 8H), 1.40-1.02 (m, 5H); RP-HPLC tR=5.91 min; ESI-MS m/z 265.2 [M+H]+.

후처리

  1. customgave
  2. customYield (0.13 g, 43%)

출처 및 근거

ORD 기록
ord-d364b0c9c76740a195264120bee4dcfa
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447078B2

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