Diisopropylethylamine → HCID 76901360, compound

HRID 880327Notes

Reaction equation

[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

Participants

Conditions

Temperature: 22 °C

Procedure

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).

Workup

extractionextracted with EA
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customthe residue was was purified by prep-HPLC

Sources & evidence

ORD record: ord-2ebaef3ae7704d0588e5d8ba980e849f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993555B2

Reaction notes

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