Triethylamine → HCID 68807152、化合物

HRID 411282

反応式

HRID 411282 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 68807152HCID 68807152、化合物収率 89%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-e78ab4ca0d1b4f7f9a608a1633d02ea5
出典データセット
uspto-grants-2003_05
特許番号
US06559159B2

関連ノート

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