Dimethylamine → 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 dimethylamide

HRID 1625447Notes

Reaction equation

HRID 1625447 reaction equation
FC1C=C(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)[C:7]1=O.[F:39][C:40]1[CH:41]=[C:42]([CH:73]=[CH:74][C:75]=1[F:76])[CH2:43][N:44]1[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([NH:52][CH2:53][C:54]2[CH:55]=[C:56]([C:60]3[C:68]4[C:63](=[N:64][CH:65]=[C:66]([C:69]([OH:71])=O)[CH:67]=4)[NH:62][CH:61]=3)[CH:57]=[CH:58][CH:59]=2)=[O:51])[C:45]1=[O:72].CNC.O1CCCC1>>[CH3:5][N:6]([CH3:7])[C:69]([C:66]1[CH:67]=[C:68]2[C:60]([C:56]3[CH:57]=[CH:58][CH:59]=[C:54]([CH2:53][NH:52][C:50]([C:46]4[C:45](=[O:72])[N:44]([CH2:43][C:42]5[CH:73]=[CH:74][C:75]([F:76])=[C:40]([F:39])[CH:41]=5)[CH:49]=[CH:48][CH:47]=4)=[O:51])[CH:55]=3)=[CH:61][NH:62][C:63]2=[N:64][CH:65]=1)=[O:71]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 593624353-[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 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 593625743-[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 dimethylamide

Procedure

Except where indicated, 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 dimethylamide 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-[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 (53 mg, 0.00010 mol) as carboxylic acid and 2.00 M of dimethylamine in tetrahydrofuran (127 uL, 0.254 mmol; Aldrich) as amine, to yield the product. 1H NMR (400 MHz, CDCl3-MeOH-d4) d ppm 8.751 (m, 1H) 8.481 (m, 1H) 8.424 (m, 1H) 7.755 (m, 1H) 7.562 (m, 1H) 7.525 (m, 1H) 7.454-7.379 (m, 2H) 7.342 (m, 1H) 7.138-7.032 (m, 2H) 7.005-6.936 (m, 1H) 6.450 (m, 1H) 5.096 (m, 2H) 4.640 (m, 2H) 3.082 (m, 6H); MS m/z=542.33 M+H.

Workup

  1. customto yield the product

Sources & evidence

ORD record
ord-2bf434f99b9d4740a987377d8ca45da6
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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