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Ammonia → (1S,5S)-3-(5,6-Dichloro-pyridin-3-yl)-3,6-diaza-bicyclo[3.2.0]heptane fumarate

HRID 495100
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HRID 495100 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:15][C@@H:14]3[C@@H:11]([CH2:12][NH:13]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8].[C:16]([OH:23])(=[O:22])/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20].O.N>C1COCC1.CO>[C:16]([OH:23])(=[O:22])/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:15][C@@H:14]3[C@@H:11]([CH2:12][NH:13]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8]
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참가 물질

7

반응물 4

HCID 222AmmoniaHCID 962WaterHCID 444972Fumaric AcidHCID 10131048Sofinicline

생성물 1

HCID 11639080(1S,5S)-3-(5,6-Dichloro-pyridin-3-yl)-3,6-diaza-bicyclo[3.2.0]heptane fumarate

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

Under N2, to a solution of the product of Example 5J (122 mg, 0.5 mmol) in THF (5 mL) was slowly added the solution of fumaric acid (70 mg, 0.6 mmol) in MeOH (0.6 mL). The mixture was then stirred at ambient temperature for 6 h. White solid started to precipitate. The solid was then filtered and dried (150 mg, yield, 84%). M.p. 198-202° C. Solubility: 2.9 mg/mL (water). 1H NMR (CD3OD, 300 MHZ) δ 3.07 (dd, J=10.5, 6.5 Hz, 1H), 3.17 (dd, J=12.2, 4.7 Hz, 1H), 3.44-3.55 (m, 1H), 3.71 (dd, J=10.5, 4.8 Hz, 1H), 3.90 (d, J=10.5 Hz, 1H), 4.11 (d, J=12.2 Hz, 1H), 4.26 (dd, J=10.9, 8.5 Hz, 1H), 5.04 (dd, J=7.2, 5.1 Hz, 1H), 6.68 (s, 2H), 7.53 (d, J=3.1 Hz, 1H), 7.96 (d, J=2.7 Hz, 1H) ppm. MS (DCI/NH3) m/z 244 (M+H)+, 246 (M+H)+.

후처리

  1. customto precipitate
  2. filtrationThe solid was then filtered
  3. customdried
  4. custom(150 mg, yield, 84%)

출처 및 근거

ORD 기록
ord-8a0c693a00d54b5ebb3db6fb59ab271c
출처 데이터셋
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07538226B2

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