3-Fluorobenzoic Acid → HCID 89466085, compound

HRID 1184577Notes

Reaction equation

HRID 1184577 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]3[CH2:15][CH2:16][CH:17]([NH2:18])[CH:11]3[CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](O)=[O:26].OC1C2N=NNC=2C=CC=1.CN(C)CCCN=C=NCC>ClCCl>[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([NH:18][C@H:17]1[C@@H:11]2[CH2:10][N:9]([C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:19])[F:20])[N:8]=3)[CH2:14][CH2:13][N:12]2[CH2:15][CH2:16]1)=[O:26]

Participants

6

Reactant 4

HCID 99683-Fluorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 89466349HCID 89466349, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 89466085HCID 89466085, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 96B (100 mg, 0.349 mmol), 3-fluorobenzoic acid (58.7 mg, 0.419 mmol) and hydroxybenzotriazole (58.8 mg, 0.384 mmol) in dichloromethane (1.5 mL), was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.067 mL, 0.384 mmol). The mixture was stirred at room temperature overnight. The mixture was then purified via HPLC (Gilson®, XBridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=250 nm) to give the title compound as the first eluting diastereomer. 1H NMR (500 MHz, methanol-d4) δ ppm 1.74-1.81 (m, 1 H), 2.19-2.25 (m, 1 H), 2.34 (td, 1H, J=11, 3 Hz), 2.38-2.44 (m, 1 H), 2.49 (m, 1H), 2.83 (dd, 1H, J=12, 10 Hz), 2.98-3.06 (m, 1 H), 3.08-3.18 (m, 2 H), 4.31-4.40 (m, 2 H), 4.51-4.57 (m, 1 H), 6.96 (d, 1H, J=7 Hz), 6.99 (d, 1H, J=8 Hz), 7.29 (td, 1H, J=8, 1 Hz), 7.49 (td, 1H, J=8, 6 Hz), 7.59 (dt, 1H, J=9, 2 Hz), 7.63-7.70 (m, 2 H); MS (DCI) m/z 409 (M+H)+.

Workup

  1. customThe mixture was then purified via HPLC (Gilson®, XBridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=250 nm)

Sources & evidence

ORD record
ord-b59c3ffa03cd49a7a80f34676a555103
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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