1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid → HCID 11717135, compound

HRID 2377064Notes

Reaction equation

HRID 2377064 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([OH:18])=O)[CH:15]=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.Cl.[OH:22][CH2:23][CH2:24][CH2:25][NH:26][OH:27]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([N:26]([OH:27])[CH2:25][CH2:24][CH2:23][OH:22])=[O:18])[CH:15]=[C:10]3[CH:9]=[CH:8]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 218922071-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acidHCID 86079681HCID 86079681, compound

Product 1

HCID 11717135HCID 11717135, compound

Procedure

The title compound was prepared by coupling of 1-(4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid with N-(3-hydroxypropyl)hydroxylamine hydrochloride in a manner similar to step 8 of example 1. 1H NMR (CD3OD) δ ppm 8.71 (s, 1H), 8.20 (s, 1H), 7.71 (d, 1H, J=3.0 Hz), 7.26 (m, 2H), 7.05 (d, 2H, J=8.9 Hz), 6.75 (d, 1H, J=3.0 Hz), 5.55 (s, 2H), 3.90 (m, 2H), 3.65 (t, 2H, J=6.0 Hz), 1.94-2.00 (m, 2H). LCMS (API-ES, M+H+): 344.1. HRMS calcd for C18H19FN3O3 (M+H) 344.1405, found 344.1402. HPLC: 99.1% purity.

Sources & evidence

ORD record
ord-82f31da852e845f3a2117f76baf126bc
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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