Morpholine → HCID 66830529, compound

HRID 1041097Notes

Reaction equation

HRID 1041097 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH3:11].[NH:12]1[CH2:17]COC[CH2:13]1.CC1C=C([N+]([O-])=O)C=C[C:20]=1[N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CC1C=C(N)C=CC=1N1CC[O:44][CH2:43]C1.Cl[C:49]1[N:54]=[C:53]([NH:55][C:56]2[CH:61]=[CH:60][C:59]([N:62]3[CH2:67][CH2:66][O:65][CH2:64][CH2:63]3)=[C:58]([CH3:68])[CH:57]=2)[C:52]([Cl:69])=[CH:51][N:50]=1>>[Cl:69][C:52]1[C:53]([NH:55][C:56]2[CH:61]=[CH:60][C:59]([N:62]3[CH2:67][CH2:66][O:65][CH2:64][CH2:63]3)=[C:58]([CH3:68])[CH:57]=2)=[N:54][C:49]([NH:8][C:5]2[C:6]([O:44][CH3:43])=[CH:7][C:2]3[CH2:32][CH2:33][N:28]([CH2:29][C:30]([N:12]([CH3:17])[CH3:13])=[O:31])[CH2:20][CH2:11][C:3]=3[CH:4]=2)=[N:50][CH:51]=1

Participants

6

Reactant 5

HCID 8083MorpholineHCID 83315Benzene, 1-chloro-2-methyl-4-nitro-HCID 106077873-Methyl-4-morpholinoanilineHCID 107990424-(2-Methyl-4-nitrophenyl)morpholineHCID 86633929HCID 86633929, compound

Product 1

HCID 66830529HCID 66830529, compound

Procedure

1-Chloro-2-methyl-4-nitro-benzene using Morpholine was converted in an analogous manner to Example 171b, to 4-(2-Methyl-4-nitro-phenyl)-morpholine which was converted in an analogous manner to Example 31f, to 3-Methyl-4-morpholin-4-yl-phenylamine, which was converted, in an analogous manner to Example 1d, to (2,5-Dichloro-pyrimidin-4-yl)-(3-methyl-4-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 white solid (0.041 g, 36%). MP: 252-256° C. 1HNMR (400 MHz, CDCl3, δ, ppm): 8.04 (s, 2H), 7.57-7.53 (m, 1H), 7.48 (s, 1H), 7.24-7.21 (m, 1H), 7.03 (d, 1H, J=8.6 Hz), 6.91 (s, 1H), 6.61 (s, 1H), 3.89-3.85 (m, 4H), 3.85 (s, 3H), 3.26 (s, 2H), 3.13 (s, 3H), 2.94-2.89 (m, 4H), 2.89-2.83 (m, 2H), 2.76-2.60 (m, 6H), 2.31 (s, 3H). MS: 580.27 (MH)+.

Sources & evidence

ORD record
ord-a51ef071cefb411192d366f74f2cc945
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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