Triethylamine → HCID 68807152, 화합물

HRID 411282

반응식

HRID 411282 반응식
CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[NH2:28][CH:29]1[CH2:36][CH:35]2[CH2:37][C:31]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([OH:54])[CH:49]=3)([CH:32]([CH3:47])[CH2:33][N:34]2[CH2:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:30]1.Cl.[CH3:56][N:57]([CH3:64])[CH2:58][CH2:59][CH2:60][C:61](O)=[O:62].C(N(CC)CC)C>C1COCC1.CCOCC>[CH3:56][N:57]([CH3:64])[CH2:58][CH2:59][CH2:60][C:61]([NH:28][C@H:29]1[CH2:36][C@H:35]2[CH2:37][C@:31]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([OH:54])[CH:49]=3)([C@H:32]([CH3:47])[CH2:33][N:34]2[CH2:38][CH2:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:30]1)=[O:62]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 18540869HCID 18540869, 화합물

생성물 1

HCID 68807152HCID 68807152, 화합물수율 89%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

BOP reagent (27 mg, 0.060 mmol) was added to a solution of (+)-7-amino-4-methyl-5-(3 -hydroxyphenyl)-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonane (23, 20 mg, 0.055 mmol), 4-(dimethylamino)butyric acid hydrochloride (18 mg, 0.11 mmol) and triethylamine (0.038 mL, 0.27 mmol) in dry THF (5 mL). The reaction mixture was stirred under N2 at room temperature for 4 h. The mixture was diluted with Et2O (20 mL), washed with saturated NaHCO3, followed by water, organic layer collected, dried (Na2SO4) and solvent removed under reduced pressure yielding crude product. This was purified by flash chromatography (33% (80% CHCl3:18% CH3OH:2% NH4OH) in CHCl3) to afford 4-(dimethylamino)-N-[(1R,4S,5S,7R)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicyclo[3.3.1]non-7-yl]butanamide (13) (23 mg, 89%) as an off-white foam. 1H-NMR (CDCl3) δ7.28-7.09 (m, 6H), 6.89 (d, 1H, J=7.0 Hz), 6.64-6.59 (m, 3H), 6.31 (m, 1H), 4.65 (br., 1H), 3.16 (br., 1H), 3.02 (d, 1H, J=7.8 Hz), 2.69-2.14 (m, 16H), 1.91 (m, 1H), 1.86-1.75 (m, 4H), 1.58 (m 1H), 1.36-0.83 (m, 3H), 0.71 (d, 3H, J=6.5 Hz); LRMS (ES) m/z 478.7 (M+H)+.

후처리

  1. washwashed with saturated NaHCO3
  2. customcollected
  3. dry with materialdried (Na2SO4) and solvent
  4. customremoved under reduced pressure
  5. customyielding crude product
  6. customThis was purified by flash chromatography (33% (80% CHCl3:18% CH3OH:2% NH4OH) in CHCl3)

출처 및 근거

ORD 기록
ord-e78ab4ca0d1b4f7f9a608a1633d02ea5
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559159B2

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