Benzylamine → HCID 178522798, compound

HRID 711320Notes

Reaction equation

HRID 711320 reaction equation
O[C@@H](C1C=CC=CC=1)CNC1C=CNC(=O)C=1C1NC2C(C(O)=O)=CC=CC=2N=1.C(N)C1C=CC=CC=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.F[C:72]1[CH:73]=[C:74]([CH:105]=[CH:106][CH:107]=1)[CH2:75][NH:76][C:77]([C:79]1[C:87]2[NH:86][C:85]([C:88]3[C:89](=[O:104])[NH:90][CH:91]=[CH:92][C:93]=3[NH:94][CH2:95][C@@H:96]([OH:103])[C:97]3[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=3)=[N:84][C:83]=2[CH:82]=[CH:81][CH:80]=1)=[O:78]>CN(C=O)C>[CH2:75]([NH:76][C:77]([C:79]1[C:87]2[NH:86][C:85]([C:88]3[C:89](=[O:104])[NH:90][CH:91]=[CH:92][C:93]=3[NH:94][CH2:95][C@@H:96]([OH:103])[C:97]3[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=3)=[N:84][C:83]=2[CH:82]=[CH:81][CH:80]=1)=[O:78])[C:74]1[CH:105]=[CH:106][CH:107]=[CH:72][CH:73]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178522847HCID 178522847, compoundHCID 178524247HCID 178524247, compound

Product 1

HCID 178522798HCID 178522798, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[4-((S)-2-Hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid benzylamide was synthesized from 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid, benzylamine, DIEA, HATU and DMF using a similar procedure as 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid 3-fluoro-benzylamide yielding 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid benzylamide. LC/MS calcd for C28H25N5O3 (m/e) 479.0, obsd 480 (M+H). 1H NMR (tautomers 1:2; DMSO-d6): 13.38-13.52 (m, 1H), 11.14-11.38 (m, 1H), 10.33-11.02 (m, 1H), 9.18-9.43 (m, 1H), 7.69-7.99 (m, 2H), 7.15-7.61 (m, 12H), 6.12-6.30 (m, 1H), 5.74-5.99 (m, 1H), 4.52-4.96 (m, 3H), 3.49-3.30 (m, 2H).

Sources & evidence

ORD record
ord-026a2a1b1dab419c9a119719d1151b8a
Source dataset
uspto-grants-2015_11
Patent number
US09181218B2

Reaction notes

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