Triethylamine → N-(2-hydroxy-3-(isoindolin-2-yl)propyl)-3-(pyridin-2-yl)benzamide

HRID 1507037Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[NH2:44][CH2:45][CH:46]([OH:57])[CH2:47][N:48]1[CH2:56][C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH2:49]1>C(Cl)Cl>[OH:57][CH:46]([CH2:47][N:48]1[CH2:49][C:50]2[C:55](=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:56]1)[CH2:45][NH:44][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(pyridin-2-yl)benzoic acid (60 mg, 0.30 mmol) in DCM (8 mL) was added EDCI (86 mg, 0.45 mmol), HOBt (61 mg, 0.45 mmol), Et3N (61 mg, 0.6 mmol) and 1-amino-3-(isoindolin-2-yl)propan-2-ol (86 mg, 0.45 mmol). The mixture was stirred at 25° C. for 16 h, washed with water and extracted with DCM. The combined organic extracts were concentrated, and the residue was purified by preparative HPLC purification. (30 mg, 27%) MS (ESI+) e/z: 374.2 [M+1]+. 1H NMR (MeOD, 400 MHz), δ ppm: 8.65 (d, J=4.8 Hz, 1H), 8.15 (d, J=8.0 Hz, 1H), 7.96-7.92 (m, 3H), 7.62 (dd, J=7.2 Hz, 1H), 7.40-7.35 (m, 6H), 4.70 (s, 4H), 4.29 (br.s, 1H), 3.63-3.30 (m, 4H).

Workup

washwashed with water
extractionextracted with DCM
concentrationThe combined organic extracts were concentrated
customthe residue was purified by preparative HPLC purification

Sources & evidence

ORD record: ord-b7dfe44eb5ac453fbb6e9f8e067de47e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221794B2

Reaction notes

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