HCID 57522618, compound → 2-{5-Chloro-2-[7-(2,2-difluoro-ethylamino)-2-methoxy-6,7,8,9-tetrahydro-5h-benzocyclohepten-1-ylamino]-pyrimidin-4-ylamino}-n-methyl-benzamide

HRID 1687551Notes

Reaction equation

HRID 1687551 reaction equation
ClC1N=C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)C(Cl)=CN=1.Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=2[C:30]([NH:32][CH3:33])=[O:31])[C:24]([Cl:38])=[CH:23][N:22]=1.COC1C(N)=CC2CCC(N3CCOCC3)CCC=2C=1.[F:59][CH:60]([F:77])[CH2:61][NH:62][CH:63]1[CH2:69][CH2:68][C:67]2=[C:70]([NH2:76])[C:71]([O:74][CH3:75])=[CH:72][CH:73]=[C:66]2[CH2:65][CH2:64]1>>[Cl:38][C:24]1[C:25]([NH:27][C:28]2[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=2[C:30]([NH:32][CH3:33])=[O:31])=[N:26][C:21]([NH:76][C:70]2[C:67]3[CH2:68][CH2:69][CH:63]([NH:62][CH2:61][CH:60]([F:77])[F:59])[CH2:64][CH2:65][C:66]=3[CH:73]=[CH:72][C:71]=2[O:74][CH3:75])=[N:22][CH:23]=1

Participants

5

Reactant 4

HCID 57522618HCID 57522618, compoundHCID 575226243-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamineHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 131729604N*7*-(2,2-Difluoro-ethyl)-2-methoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene-1,7-diamine

Product 1

HCID 251587592-{5-Chloro-2-[7-(2,2-difluoro-ethylamino)-2-methoxy-6,7,8,9-tetrahydro-5h-benzocyclohepten-1-ylamino]-pyrimidin-4-ylamino}-n-methyl-benzamide

Procedure

Prepared in an analogous fashion to Example 1047 replacing (1S,2S,3R,4R)-3-(2,5-Dichloro-pyrimidin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide with 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide and 3-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine was replaced with N*7*-(2,2-Difluoro-ethyl)-2-methoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene-1,7-diamine to afford 2-{5-Chloro-2-[7-(2,2-difluoro-ethylamino)-2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide. LC/MS (ESI): 531.23. 1H NMR (400 MHz, DMSO, d6) δ 9.07 (m, 2H), 8.87 (m, 1H), 8.74 (m, 1H), 8.16 (m, 1H), 8.01 (m, 1H), 7.71 (m, 1H), 7.01 (m, 2H), 6.89 (m, 1H), 6.38 (td, 1H), 3.78 (s, 3H), 3.55 (m, 2H), 3.38 (m, 1H), 3.07 (m, 1H), 2.79 (s, 3H), 2.68-2.86 (m, 2H), 2.32 (m, 3H), 1.33 (m, 2H).

Sources & evidence

ORD record
ord-023f3a1ea60341f29dec5532f8281481
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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