4-Methylmorpholine → 1h-Pyrrolo[2,3-c]pyridine-5-carboxamide,1-[(4-fluorophenyl)methyl]-n-hydroxy-n-methyl-3-[[(tetrahydro-2h-pyran-4-yl)oxy]methyl]-

HRID 2377113

Reaction equation

HRID 2377113 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][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[C:9]([CH2:19][O:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:8]2)=[CH:4][CH:3]=1.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.Cl.[CH3:48][NH:49][OH:50]>>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([N:49]([OH:50])[CH3:48])=[O:18])[CH:15]=[C:10]3[C:9]([CH2:19][O:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 77906N-methylhydroxylamine hydrochlorideHCID 598558511h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-3-[[(tetrahydro-2h-pyran-4-yl)oxy]methyl]-

Product 1

HCID 159570831h-Pyrrolo[2,3-c]pyridine-5-carboxamide,1-[(4-fluorophenyl)methyl]-n-hydroxy-n-methyl-3-[[(tetrahydro-2h-pyran-4-yl)oxy]methyl]-

Procedure

The title compound was prepared as in example 116, step 3, using 1-(4-fluorobenzyl)-3-[(tetrahydro-2H-pyran-4-yloxy)methyl]-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid, 2-chloro-4,6-dimethoxy-1,3,5-triazine, N-methyl morpholine, and N-methyl hydroxylamine hydrochloride. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.38-1.48 (m, 2H) 1.84-1.91 (m, 2H) 3.28-3.37 (m, J=10.74, 10.74, 2.78 Hz, 5H) 3.60 (ddd, J=8.84, 4.80, 4.55 Hz, 1H) 3.80 (ddd, J=11.49, 4.29, 4.17 Hz, 2H) 4.69 (s, 2H) 5.54 (s, 2H) 7.16 (t, J=8.97 Hz, 2H) 7.36 (dd, J=8.72, 5.43 Hz, 2H) 7.86 (s, 1H) 8.03 (s, 1H) 8.89 (s, 1H)

Sources & evidence

ORD record
ord-ca0c34184a93408d8a77fb68150f869f
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Linked notes

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