HCID 57522618, compound → HCID 86633933, compound

HRID 1687408Notes

Reaction equation

HRID 1687408 reaction equation
[F:1][CH:2]([F:18])[CH2:3][N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[C:12]([NH2:17])[C:13]([O:15][CH3:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1.Cl[C:20]1[N:25]=[C:24]([NH:26][C@@H:27]2[C@@H:32]3[CH2:33][C@@H:29]([CH:30]=[CH:31]3)[C@@H:28]2[C:34]([NH2:36])=[O:35])[C:23]([Cl:37])=[CH:22][N:21]=1>>[Cl:37][C:23]1[C:24]([NH:26][C@@H:27]2[C@@H:32]3[CH2:33][C@@H:29]([CH:30]=[CH:31]3)[C@@H:28]2[C:34]([NH2:36])=[O:35])=[N:25][C:20]([NH:17][C:12]2[C:13]([O:15][CH3:16])=[CH:14][C:7]3[CH2:6][CH2:5][N:4]([CH2:3][CH:2]([F:1])[F:18])[CH2:10][CH2:9][C:8]=3[CH:11]=2)=[N:21][CH:22]=1

Participants

3

Reactant 2

HCID 57522618HCID 57522618, compoundHCID 866339233-(2,2-Difluoro-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine

Product 1

HCID 86633933HCID 86633933, compound

Procedure

The title compound was prepared from 3-(2,2-Difluoro-ethyl)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine and (1S,2S,3R,4R)-3-(2,5-Dichloro-pyrimidin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide in an analogous manner to Example 61e. Product isolated as an off-white solid (0.025 g, 48%). MP: 127-147° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.18 (s, 1H), 7.89 (s, 1H), 7.40 (s, 1H), 6.63 (s, 1H), 6.57 (d, 1H, J=8.3 Hz), 6.32-6.29 (m, 2H), 6.07-5.75 (m, 1H), 5.56 (s, 1H), 5.32 (s, 1H), 4.45 (t, 1H, J=8.3 Hz), 3.86 (s, 3H), 3.07 (s, 1H), 2.97-2.77 (m, 11H), 2.51 (d, 1H, J=8.0 Hz), 2.26 (d, 1H, J=9.1 Hz), 1.68-1.63 (m, 1H). MS: 519.18 (MH)+.

Sources & evidence

ORD record
ord-58bd91c1e35140a5b2070eaee32da581
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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