HCID 57522618, compound → N-{(1R,2R)-2-[5-Chloro-2-(2-methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide

HRID 1041235Notes

Reaction equation

HRID 1041235 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@@H:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]2[NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:24]([Cl:39])=[CH:23][N:22]=1.COC1C(N)=CC2CCC(N3CCOCC3)CCC=2C=1.[CH3:60][O:61][C:62]1[CH:63]=[CH:64][C:65]2[CH2:71][CH2:70][CH:69]([N:72]3[CH2:77][CH2:76][O:75][CH2:74][CH2:73]3)[CH2:68][CH2:67][C:66]=2[C:78]=1[NH2:79]>>[Cl:39][C:24]1[C:25]([NH:27][C@@H:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C@H:29]2[NH:34][S:35]([CH3:38])(=[O:37])=[O:36])=[N:26][C:21]([NH:79][C:78]2[C:66]3[CH2:67][CH2:68][CH:69]([N:72]4[CH2:73][CH2:74][O:75][CH2:76][CH2:77]4)[CH2:70][CH2:71][C:65]=3[CH:64]=[CH:63][C:62]=2[O:61][CH3:60])=[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 672640572-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamineHCID 86633854N-[(1R,2R)-2-(2,5-dichloropyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide

Product 1

HCID 67264096N-{(1R,2R)-2-[5-Chloro-2-(2-methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide

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 N-[(1R,2R)-2-(2,5-Dichloro-pyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide and 3-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine was replaced with 2-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamine to afford N-{(1R,2R)-2-[5-Chloro-2-(2-methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamino)-pyrimidin-4-ylamino]-cyclohexyl}-methanesulfonamide (Diasteromeric Mix). LC/MS (ESI): 579.24. 1H NMR (400 MHz, DMSO, d6) δ 9.85 (m, 1H), 7.17 (m, 1H), 6.88 (m, 1H), 3.94 (m, 3H), 3.70 (s, 3H), 3.28 (m, 3H), 3.20 (m, 6H), 2.88 (s, 3H), 2.72 (m, 2H), 1.99 (m, 4H), 1.67 (m, 2H), 1.41 (m, 2H), 1.21 (m, 5H).

Sources & evidence

ORD record
ord-5f6c99fcbbb44b659cca26996fdf304a
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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