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,n-dimethyl-benzenesulfonamide

HRID 1687550Notes

Reaction equation

HRID 1687550 reaction equation
Cl[C:2]1N=C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)C(Cl)=[CH:4][N:3]=1.Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34](C(C)C)(=[O:36])=[O:35])[C:24]([Cl:40])=[CH:23][N:22]=1.COC1C(N)=CC2CCC(N3CCOCC3)CCC=2C=1.[F:61][CH:62]([F:79])[CH2:63][NH:64][CH:65]1[CH2:71][CH2:70][C:69]2=[C:72]([NH2:78])[C:73]([O:76][CH3:77])=[CH:74][CH:75]=[C:68]2[CH2:67][CH2:66]1>>[Cl:40][C:24]1[C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[S:34]([N:3]([CH3:4])[CH3:2])(=[O:35])=[O:36])=[N:26][C:21]([NH:78][C:72]2[C:69]3[CH2:70][CH2:71][CH:65]([NH:64][CH2:63][CH:62]([F:79])[F:61])[CH2:66][CH2:67][C:68]=3[CH:75]=[CH:74][C:73]=2[O:76][CH3:77])=[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 597643782,5-dichloro-N-(2-((1-methylethyl)sulfonyl)phenyl)-4-pyrimidinamineHCID 131729604N*7*-(2,2-Difluoro-ethyl)-2-methoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene-1,7-diamine

Product 1

HCID 251587602-{5-Chloro-2-[7-(2,2-difluoro-ethylamino)-2-methoxy-6,7,8,9-tetrahydro-5h-benzocyclohepten-1-ylamino]-pyrimidin-4-ylamino}-n,n-dimethyl-benzenesulfonamide

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 (2,5-Dichloro-pyrimidin-4-yl)-[2-(propane-2-sulfonyl)-phenyl]-amine 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,N-dimethyl-benzenesulfonamide. LC/MS (ESI): 581.24. 1H NMR (400 MHz, DMSO, d6) δ 9.46 (s, 1H), 8.99 (m, 2H), 8.08 (m, 2H), 7.72 (m, 1H), 7.13 (m, 3H), 6.85 (m, 1H), 6.38 (td, 1H), 3.66 (s, 3H), 3.54 (m, 2H), 3.39 (m, 1H), 3.06 (m, 1H), 2.84 (m, 1H), 2.66 (s, 6H), 2.29 (m, 4H), 1.31 (m, 2H).

Sources & evidence

ORD record
ord-4d54d272623646859abdfaeaa9cefc8b
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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