Trifluoroacetic acid → HCID 67263998, compound

HRID 1687486Notes

Reaction equation

HRID 1687486 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([NH2:17])[CH:15]=[CH:16][C:9]=2[CH2:8][CH2:7]1.Cl[C:19]1[N:24]=[C:23]([NH:25][C@@H:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:22]([Cl:37])=[CH:21][N:20]=1.[C:38](O)(C(F)(F)F)=[O:39]>>[Cl:37][C:22]1[C:23]([NH:25][C@@H:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C@H:27]2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[N:24][C:19]([NH:17][C:14]2[C:15]([O:39][CH3:38])=[CH:16][C:9]3[CH2:8][CH2:7][CH:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:12][CH2:11][C:10]=3[CH:13]=2)=[N:20][CH:21]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67263696HCID 67263696, compoundHCID 86633854N-[(1R,2R)-2-(2,5-dichloropyrimidin-4-ylamino)-cyclohexyl]-methanesulfonamide

Product 1

HCID 67263998HCID 67263998, compound

Procedure

The title compound was prepared from N(7)-(2-methoxyethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine and N[(1R,2R)-2-(2,5-dichloropyrimidin-4-ylamino)-cyclohexyl]methanesulfonamide in an analogous manner to Example 179. Product was prepared as a TFA salt (16.6 mg, 21%). LCMS (m/e) 567 (M+H); 1H NMR (400 MHz, CDCl3) 9.89 (broad s, 1H), 9.03 (broad s, 1H), 8.03 (s, 1H), 7.54 (broad s, 1H), 7.20 (s, 2H), 6.46 (s, 1H), 3.82 (s, 1H), 3.67 (s, 5H), 3.36 (m, 5H), 3.19 (s, 2H), 3.02 (s, 3H), 2.61-2.86 (m, 4H), 2.34 (m, 2H), 2.17 (m, 1H), 2.08 (d, 1H, J=11.37 Hz), 1.85 (d, 1H, J=12.3 Hz), 1.72 (m, 1H), 1.59 (m, 3H), 1.32 (m, 1H), 1.13 (m, 2H).

Sources & evidence

ORD record
ord-68ee814ca3cb43cb9bd00bbb460c9c61
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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