Ethylamine hydrochloride → 3-[5-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-thiophen-2-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethylamide

HRID 1625451Notes

Reaction equation

HRID 1625451 reaction equation
FC1C=[C:4](C=CC=1F)[CH2:5][N:6]1C=CC=C(C(NCC2C=C(C3C4C(=NC=C(C(N)=O)C=4)NC=3)C=CC=2)=O)C1=O.[F:39][C:40]1[CH:41]=[C:42]([CH:72]=[CH:73][C:74]=1[F:75])[CH2:43][N:44]1[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([NH:52][CH2:53][C:54]2[S:58][C:57]([C:59]3[C:67]4[C:62](=[N:63][CH:64]=[C:65]([C:68]([OH:70])=O)[CH:66]=4)[NH:61][CH:60]=3)=[CH:56][CH:55]=2)=[O:51])[C:45]1=[O:71].Cl.C(N)C>>[CH2:5]([NH:6][C:68]([C:65]1[CH:66]=[C:67]2[C:59]([C:57]3[S:58][C:54]([CH2:53][NH:52][C:50]([C:46]4[C:45](=[O:71])[N:44]([CH2:43][C:42]5[CH:72]=[CH:73][C:74]([F:75])=[C:40]([F:39])[CH:41]=5)[CH:49]=[CH:48][CH:47]=4)=[O:51])=[CH:55][CH:56]=3)=[CH:60][NH:61][C:62]2=[N:63][CH:64]=1)=[O:70])[CH3:4]

Participants

4

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 593623553-[5-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-thiophen-2-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acidHCID 593625603-[3-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid amide

Product 1

HCID 593623323-[5-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-thiophen-2-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethylamide

Procedure

Except where indicated, 3-[5-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-thiophen-2-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid ethylamide was synthesized as per Example 81, 3-[3-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-phenyl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid amide using 3-[5-({[1-(3,4-Difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-thiophen-2-yl]-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (43 mg, 0.000083 mol) as carboxylic acid and ethylamine hydrochloride (17 mg, 0.00021 mol; Aldrich) as amine, to yield the product. 1H NMR (400 MHz, DMSO-d6) d ppm 12.161 (s, 1H) 10.066 (t, J=5.6 Hz, 1H) 8.760 (s, 1H) 8.634 (s, 1H) 8.606 (m, 1H) 8.404 (d, J=7.4 Hz, 1H) 8.237 (d, J=6.5 Hz, 1H) 7.855 (s, 1H) 7.479-7.347 (m, 2H) 7.272 (d, J=3.0 Hz, 1H) 7.187-7.129 (m, 1H) 7.055 (d, J=3.0 Hz, 1H) 6.597 (t, J=7.1 Hz, 1H) 5.195 (s, 2H) 4.686 (d, J=5.9 Hz, 2H) 3.324 (qd, J=6.5 Hz, 6.5 Hz, 2H) 1.147 (t, J=6.8 Hz, 3H); MS m/z=548.19 M+H.

Workup

  1. customto yield the product

Sources & evidence

ORD record
ord-62a64e4420a448a4b0411394f52540be
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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