Diisopropylethylamine → HCID 76901360、化合物

HRID 880327ノート

反応式

HRID 880327 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:50][CH2:51][CH:52]([OH:64])[CH2:53][N:54]1[CH2:63][CH2:62][C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH2:55]1>CN(C=O)C.O>[CH2:55]1[C:56]2[C:61](=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH2:62][CH2:63][N:54]1[CH2:53][CH:52]([OH:64])[CH2:51][NH:50][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([O:7][CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 242295194-[(Oxan-4-yl)oxy]benzoic acid

生成物 1

HCID 76901360HCID 76901360、化合物収率 74.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
22 °C

実験手順

To a solution of 4-((tetrahydro-2H-pyran-4-yl)oxy)benzoic acid (150 mg, 0.67 mmol) in DMF (4 mL) was added DIEA (260 mg, 2.01 mmol), HATU (384 mg, 1.01 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (170 mg, 0.81 mmol). The reaction mixture was stirred at 22° C. for 16 h. The mixture was treated with water and extracted with EA. The organic layer was washed with brine, dried over Na2SO4, concentrated and the residue was was purified by prep-HPLC to give the title compound (206.1 mg, Yield 74.9%). 1H NMR (CD3OD, 400 MHz): δ 7.84 (d, J=8.8 Hz, 2H), 7.26-7.37 (m, 3H), 7.19-7.25 (m, 1H), 7.05 (d, J=8.8 Hz, 2H), 4.59-4.74 (m, 2H), 4.31-4.49 (m, 2H), 3.93-4.01 (m, 2H), 3.86 (brs, 1H), 3.63 (ddd, J=11.7, 8.8, 3.0 Hz, 2H), 3.53 (qd, J=14.0, 5.7 Hz, 3H), 3.37-3.44 (m, 1H), 3.11-3.32 (m, 3H), 2.02-2.12 (m, 2H), 1.69-1.81 (m, 2H). LCMS (m/z): 411.2 (M+1).

後処理

  1. extractionextracted with EA
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was was purified by prep-HPLC

出典と根拠

ORDレコード
ord-2ebaef3ae7704d0588e5d8ba980e849f
出典データセット
uspto-grants-2015_03
特許番号
US08993555B2

反応ノート

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