Isopropylamine → HCID 68770231, compound

HRID 1173027Notes

Reaction equation

HRID 1173027 reaction equation
CN(C(ON1N=[N:16][C:11]2[CH:12]=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]([C:32]1[CH:33]=[C:34]([CH:49]=[CH:50][CH:51]=1)[CH2:35][NH:36][C:37]1[CH:42]=[CH:41][C:40]([C@@H:43]2[CH2:45][C@H:44]2[C:46](O)=[O:47])=[CH:39][CH:38]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N)(C)C.CCCCCC>CN(C)C=O.O.C(OCC)(=O)C>[CH3:10][CH:11]([NH:16][C:46]([C@@H:44]1[CH2:45][C@H:43]1[C:40]1[CH:39]=[CH:38][C:37]([NH:36][CH2:35][C:34]2[CH:49]=[CH:50][CH:51]=[C:32]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:33]=2)=[CH:42][CH:41]=1)=[O:47])[CH3:12]

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 8058HexaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11739868HCID 11739868, compound

Product 1

HCID 68770231HCID 68770231, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (0.159 g, 0.42 mmol) was added to a solution of (+)-(trans)-2-{4-[(3-phenoxybenzyl)amino]phenyl}cyclopropanecarboxylic acid (III-3b) (0.100 g, 0.28 mmol) in 3 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 10 minutes and 0.059 mL (0.69 mmol) of isopropylamine was added. After stirring at room temperature for 15 minutes, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated. Chromatography on silica gel with hexane:ethyl acetate gave 0.068 g (61% yield) of the title compound as a white powder. NMR (400 MHz, CDCl3) δ 7.32 (d, J=8.61 Hz, 2H), 7.28 (d, J=8.6 Hz, 2H), 7.10 (t, J=8.42 Hz, 1H), 7.00 (m, 1H), 6.97 (d, J=6.59 Hz, 2H), 6.89 (d, J=8.61 Hz, 2H), 6.87 (m, 1H), 6.52 (d, J=8.61 Hz, 2H), 5.37 (d, J=7.51 Hz, 1H), 4.27 (s, 2H), 4.10 (septet, J=6.59 Hz, 1H), 4.00 (br s, 1H), 2.36 (m, 1H), 1.52 (m, 1H), 1.40 (m, 1H), 1.15 (d, J=4.21 Hz, 3H), 1.14 (d, J=4.40 Hz, 3H), 1.10 (m, 1H). ES-MS m/z 401 (M-H)+. [α]25,D=+183° (chloroform, c=1.5).

Workup

  1. stirringAfter stirring at room temperature for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-375be05e061f420a9a8f61a7ebfafd68
Source dataset
uspto-grants-2010_11
Patent number
US07834013B2

Reaction notes

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