(5S)-6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine → HCID 59264540, compound

HRID 1950733Notes

Reaction equation

HRID 1950733 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[C:13]([Br:18])=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].ClC1C=CC2CCNC[C@@H](C)C=2C=1Cl>>[Br:18][C:13]1[C:9]2[C@H:10]([CH3:12])[CH2:11][NH:5][CH2:6][CH2:7][C:8]=2[CH:16]=[CH:15][C:14]=1[Cl:17].[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][C@@H:10]([CH3:12])[C:9]2[C:13]([Br:18])=[C:14]([Cl:17])[CH:15]=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 11608308(5S)-6,7-dichloro-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineHCID 86613110HCID 86613110, compound

Product 2

HCID 59264540HCID 59264540, compoundHCID 86613110HCID 86613110, compound

Procedure

Compound 8 was prepared from (S)—N-trifluoroacetyl-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine utilizing a similar procedure as described herein for the preparation of Compound 5. (S)-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine was obtained from (S)—N-trifluoroacetyl-9-bromo-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine. 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=8 Hz, 1H), 6.92 (d, J=8 Hz, 1H), 3.92-3.87 (m, 1H), 3.29-3.20 (m, 2H), 3.11 (dd, J=14, 5 Hz, 1H), 2.99 (dd, J=14, 2 Hz, 1H), 2.74-2.65 (m, 2H), 1.32 (d, J=7 Hz, 3H). MS calculated for C11H13BrClN+H: 274, observed: 274.

Sources & evidence

ORD record
ord-abfa6a6059d047f190c13e6ee10e64bd
Source dataset
uspto-grants-2013_03
Patent number
US08404675B2

Reaction notes

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