Morpholine → HCID 66830032, compound

HRID 1041101Notes

Reaction equation

HRID 1041101 reaction equation
FC1C=CC([N+]([O-])=O)=CC=1OC.[NH:13]1[CH2:18]COC[CH2:14]1.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([N+]([O-])=O)[CH:24]=[CH:23][C:22]=1[N:30]1CCOCC1.COC1C=C(N)C=[CH:42][C:43]=1[N:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.Cl[C:52]1[N:57]=[C:56]([NH:58][C:59]2[CH:64]=[CH:63][C:62]([N:65]3[CH2:70][CH2:69][O:68][CH2:67][CH2:66]3)=[C:61]([O:71][CH3:72])[CH:60]=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]([N:65]3[CH2:70][CH2:69][O:68][CH2:67][CH2:66]3)=[C:61]([O:71][CH3:72])[CH:60]=2)=[N:57][C:52]([NH:30][C:22]2[C:21]([O:20][CH3:19])=[CH:26][C:25]3[CH2:48][CH2:49][N:44]([CH2:45][C:46]([N:13]([CH3:18])[CH3:14])=[O:47])[CH2:43][CH2:42][C:24]=3[CH:23]=2)=[N:53][CH:54]=1

Participants

6

Reactant 5

HCID 8083MorpholineHCID 144519681-Fluoro-2-methoxy-4-nitrobenzeneHCID 219364654-(2-Methoxy-4-nitrophenyl)morpholineHCID 219364683-Methoxy-4-(morpholin-4-yl)anilineHCID 86633932HCID 86633932, compound

Product 1

HCID 66830032HCID 66830032, compound

Procedure

1-Fluoro-2-methoxy-4-nitro-benzene using Morpholine was converted in an analogous manner to Example 171b, to 4-(2-Methoxy-4-nitro-phenyl)-morpholine, which was converted in an analogous manner to Example 31f, to 3-Methoxy-4-morpholin-4-yl-phenylamine, which was converted, in an analogous procedure to Example 1d, to (2,5-Dichloro-pyrimidin-4-yl)-(3-methoxy-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 (52 mg, 0.00018 mol). Product isolated as an off-white solid (0.053 g, 48%). MP: 203-206° C. 1HNMR (400 MHz, CDCl3, δ, ppm): 8.07 (s, 1H), 8.05 (s, 1H), 7.49 (s, 1H), 7.16-7.12 (m, 1H), 7.12-7.09 (m, 1H), 6.95 (s, 1H), 6.90 (d, 1H, J=8.6 Hz), 6.61 (s, 1H), 3.93-3.89 (m, 4H), 3.85 (s, 3H), 3.80 (s, 3H), 3.26 (br s, 2H), 3.13 (s, 3H), 3.10-3.05 (m, 4H), 2.97 (s, 3H), 2.90-2.82 (m, 2H), 2.75-2.56 (m, 6H). MS: 596.24 (MH)+.

Sources & evidence

ORD record
ord-632424e40ebe4ceb834f889bfc7d692e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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