Morpholine → HCID 66830500, compound

HRID 1687424Notes

Reaction equation

HRID 1687424 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N+]([O-])=O.[NH:13]1[CH2:18]COC[CH2:14]1.COC1C=CC([N+]([O-])=O)=[C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:26]=1.COC1C=CC([NH2:44])=C(N2CCOCC2)C=1.Cl[C:52]1[N:57]=[C:56]([NH:58][C:59]2[CH:64]=[CH:63][C:62]([O:65][CH3:66])=[CH:61][C:60]=2[N:67]2[CH2:72][CH2:71][O:70][CH2:69][CH2:68]2)[C:55]([Cl:73])=[CH:54][N:53]=1>>[Cl:73][C:55]1[C:56]([NH:58][C:59]2[CH:64]=[CH:63][C:62]([O:65][CH3:66])=[CH:61][C:60]=2[N:67]2[CH2:72][CH2:71][O:70][CH2:69][CH2:68]2)=[N:57][C:52]([NH:44][C:5]2[C:6]([O:8][CH3:9])=[CH:7][C:2]3[CH2:31][CH2:32][N:27]([CH2:28][C:29]([N:13]([CH3:18])[CH3:14])=[O:30])[CH2:25][CH2:26][C:3]=3[CH:4]=2)=[N:53][CH:54]=1

Participants

6

Reactant 5

HCID 8083MorpholineHCID 5656543-Fluoro-4-nitroanisoleHCID 18952250HCID 18952250, compoundHCID 20136246HCID 20136246, compoundHCID 86633936HCID 86633936, compound

Product 1

HCID 66830500HCID 66830500, compound

Procedure

2-Fluoro-4-methoxy-1-nitro-benzene using Morpholine was converted in an analogous manner to Example 171b, to 4-(5-Methoxy-2-nitro-phenyl)-morpholine, which was converted in an analogous manner to Example 31f, to 4-Methoxy-2-morpholin-4-yl-phenylamine, which was converted, in an analogous procedure to Example 1d, to (2,5-Dichloro-pyrimidin-4-yl)-(4-methoxy-2-morpholin-4-yl-phenyl)-amine, which was converted to the title compound in an analogous manner to Example 61e using 2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N,N-dimethyl-acetamide. Product isolated as a tan foam (0.047 g, 47%). MP: 86-96° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.42 (d, 1H, J=8.8 Hz), 8.37 (s, 1H), 8.12 (s, 1H), 8.04 (s, 1H), 7.42 (s, 1H), 6.78-6.75 (m, 1H), 6.71-6.67 (m, 1H), 6.65 (s, 1H), 3.93-3.88 (m, 4H), 3.87 (s, 3H), 3.82 (s, 3H), 3.28 (s, 2H), 3.15 (s, 3H), 2.98 (s, 3H), 2.94-2.85 (m, 8H), 2.74-2.68 (m, 4H). MS: 596.50 (MH)+.

Sources & evidence

ORD record
ord-2d5e90b5a7294388b1385fce9842fabf
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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