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Hydrochloric Acid → N-(4-(Chlorodifluoromethoxy)phenyl)-6-(trans-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

HRID 924130
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HRID 924130 반응식
Cl[C:2]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[N:26][CH:27]=2)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[OH:28][CH2:29][C@@H:30]1[CH2:34][NH:33][CH2:32][C@H:31]1[OH:35].Cl.CCN(C(C)C)C(C)C>CC(O)C.O>[Cl:19][C:16]([F:18])([F:17])[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:20]=[C:21]([C:22]3[CH:23]=[N:24][CH:25]=[N:26][CH:27]=3)[C:2]([N:33]3[CH2:34][C@@H:30]([CH2:29][OH:28])[C@H:31]([OH:35])[CH2:32]3)=[N:3][CH:4]=2)=[CH:10][CH:11]=1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 11217244(3s,4s)-4-(Hydroxymethyl)pyrrolidin-3-olHCID 899064746-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(pyrimidin-5-yl)nicotinamide

생성물 1

HCID 89908027N-(4-(Chlorodifluoromethoxy)phenyl)-6-(trans-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

시약·촉매·용매

2
HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

A suspension of 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(pyrimidin-5-yl)nicotinamide (Stage 247.1, 80 mg, 0.195 mmol), trans-4-(hydroxymethyl)pyrrolidin-3-ol (+/−), hydrochloride (80 mg, 0.521 mmol) in a mixture of DIPEA (136 μL, 0.778 mmol) and iPrOH (389 μL) was subjected to MW irradiation at 140° C. for 1.5 h. The RM was treated with water (10 mL) and extracted with EtOAc. The combined extracts were washed with sat. NaHCO3 and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give a crude product that was purified by preparative SFC (Column DEAP, from 22% to 27% in 10 min) to yield the title product as a white solid. UPLC-MS (Condition 3) tR=0.86 min, m/z=492.1 [M+H]+, m/z=536.2 [M+ formic acid-H]; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.04-2.14 (m, 1H) 2.89 (dd, J=11.13, 3.91 Hz, 1H) 3.10 (dd, J=11.13, 5.26 Hz, 1H) 3.20-3.29 (m, 2H) 3.34-3.48 (m, 2H) 3.92-4.01 (m, 1H) 4.63 (t, J=5.26 Hz, 1H) 4.98 (d, J=4.40 Hz, 1H) 7.35 (d, J=9.05 Hz, 2H) 7.81-7.90 (m, 2H) 8.10 (d, J=2.45 Hz, 1H) 8.80 (d, J=2.32 Hz, 1H) 8.90 (s, 2H) 9.20 (s, 1H) 10.19 (s, 1H).

후처리

  1. customwas subjected to MW irradiation at 140° C. for 1.5 h
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with sat. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated off under reduced pressure
  6. customto give a crude product that
  7. customwas purified by preparative SFC (Column DEAP, from 22% to 27% in 10 min)

출처 및 근거

ORD 기록
ord-d11ab0292ace4be9922474c0199cf41c
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278981B2

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