2-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N-methyl-acetamide → HCID 67263319, compound

HRID 1687554Notes

Reaction equation

HRID 1687554 reaction equation
NC1C(OC)=CC2CCN(CC(NC)=O)CCC=2C=1.ClC1N=C(N[C@@H]2CCCC[C@H]2NS(C)(=O)=O)C(Cl)=CN=1.[Cl:40][C:41]1[C:42]([NH:67][C@@H:68]2[CH2:73][CH2:72][CH2:71][CH2:70][C@H:69]2[NH:74][S:75]([CH3:78])(=[O:77])=[O:76])=[N:43][C:44]([NH:47][C:48]2[C:64]([O:65][CH3:66])=[CH:63][C:51]3[CH2:52][CH2:53][N:54]([CH2:57][C:58]([N:60](C)[CH3:61])=[O:59])[CH2:55][CH2:56][C:50]=3[CH:49]=2)=[N:45][CH:46]=1>>[Cl:40][C:41]1[C:42]([NH:67][C@@H:68]2[CH2:73][CH2:72][CH2:71][CH2:70][C@H:69]2[NH:74][S:75]([CH3:78])(=[O:77])=[O:76])=[N:43][C:44]([NH:47][C:48]2[C:64]([O:65][CH3:66])=[CH:63][C:51]3[CH2:52][CH2:53][N:54]([CH2:57][C:58]([NH:60][CH3:61])=[O:59])[CH2:55][CH2:56][C:50]=3[CH:49]=2)=[N:45][CH:46]=1

Participants

4

Reactant 3

HCID 672635732-(7-Amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N-methyl-acetamideHCID 672640302-{7-[5-chloro-4-((1R,2R)-2-methanesulfonylamino-cyclohexylamino)-pyrimidin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamideHCID 86633854N-[(1R,2R)-2-(2,5-dichloropyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide

Product 1

HCID 67263319HCID 67263319, compound

Procedure

Following a procedure similar to Example 258c, 2-(7-amino-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-N-methyl-acetamide, prepared in analogous manner to Example 258a-b, and N-[(1R,2R)-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide were converted to 2-{7-[5-chloro-4-((1R,2R)-2-methanesulfonylamino-cyclohexylamino)-pyrimidin-2-ylamino]-8-methoxy-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl}-N,N-dimethyl-acetamide (42 mg, 40%) as a white solid. MP: 92-104° C.; 1H-NMR (CDCl3) δ 8.01 (s, 1H), 7.95 (s, 1H), 7.33 (br s, 1H), 7.32 (s, 1H), 6.65 (s, 1H), 5.36 (d, J=8.0 Hz, 1H), 5.27 (d, J=6.8 Hz, 1H), 3.95 (m, 1H), 3.87 (s, 3H), 3.22 (m, 1H), 3.13 (s, 2H), 2.89 (m, 4H), 2.88 (s, 3H), 2.79 (s, 3H), 2.72 (m, 4H), 2.23 (m, 2H), 1.83 (m, 2H), 1.37 (m, 2H), 0.86 (m, 2H); LC/MS (ESI+): 565.99 (M+H).

Sources & evidence

ORD record
ord-82ea1fd8e4eb408faca0b05869392c71
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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