Trifluoroacetic acid → HCID 67263998, compound

HRID 1041181Notes

Reaction equation

HRID 1041181 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-4a73a8c53cbb4ce8aed4157e1e9b056c
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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