Ammonia → HCID 69432536, compound

HRID 1793554Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([C@@H:19]4[CH2:24][NH:23][CH2:22][CH2:21][C@@H:20]4[N:15]3[CH2:14][CH2:13][CH2:12]2)[CH:18]=1.Br[CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29].N>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([C@@H:19]4[CH2:24][N:23]([CH2:26][CH:27]=[C:28]([CH3:30])[CH3:29])[CH2:22][CH2:21][C@@H:20]4[N:15]3[CH2:14][CH2:13][CH2:12]2)[CH:18]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 700922-Butene, 1-bromo-3-methyl-

HCID 9975710HCID 9975710, compound

Product 1

HCID 69432536HCID 69432536, compound

Procedure

The title compound was prepared by the method of Example 382 as a yellow oil (26 mg, 76%) from (7aS,11aR)-2-(2,4-dichlorophenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline (30 mg, 0.083 mmol) and 4-bromo-2-methyl-2-butene (25 mg, 0.16 mmol). 1H NMR (CDCl3, 300 MHz) δ 1.68 (s, 3H), 1.81 (s, 3H), 2.12–2.23 (m, 3H), 2.26–2.42 (m, 1H), 2.55–2.70 (m, 2H), 2.78 (t, J=6.6 Hz, 2H), 3.10–3.45 (m, 6H), 3.63–3.77 (m, 2H), 5.42–5.55 (br, 1H), 6.99 (s, 1H), 7.03 (s, 1H), 7.24–7.217.29 (m, 2H), 7.47 (d, J=1.8 Hz, 1H) ppm. MS (CI, NH3): 427.1 (base, M+H).

Sources & evidence

ORD record: ord-8981e0181aee476d83d906edd7021bd3
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081455B2

Reaction notes

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