Bromobenzene → (+/-)-cis-N-phenyl-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3',2',1'-ij]quinolin-2-amine

HRID 1836591Notes

Reaction equation

HRID 1836591 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:8][C:9]1[CH:10]=[C:11]2[C:16]3=[C:17]([CH2:19][CH2:20][N:15]3[CH2:14][C@@H:13]3[CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][C@H:12]23)[CH:18]=1>>[C:2]1([NH:8][C:9]2[CH:10]=[C:11]3[C:16]4=[C:17]([CH2:19][CH2:20][N:15]4[CH2:14][C@@H:13]4[CH2:21][NH:22][CH2:23][C@H:12]34)[CH:18]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7961BromobenzeneHCID 131724549(+/-)-cis tert-butyl 2-amino-4,5,7a,8,10,10a-hexahydrodipyrrolo[3,4-c:3',2',1'-ij]quinoline-9(7H)-carboxylate

Product 1

HCID 68525462(+/-)-cis-N-phenyl-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3',2',1'-ij]quinolin-2-amine

Procedure

Using bromobenzene and following the procedures described in EXAMPLE 17, Parts B and C, (±)-cis tert-butyl 2-amino-4,5,7a,8,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline-9(7H)-carboxylate was converted into (±)-cis-N-phenyl-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinolin-2-amine, bis-trifluoroacetic acid salt, after HPLC purification (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA). This material was free-based with aq ammonium hydroxide, extracted with chloroform, washed with brine, dried (K2CO3) and concentrated to the title compound of EXAMPLE 116 as the free base. 1H NMR (CDCl3) δ: 7.12 (app t, 2H, J=7.9 Hz), 6.80-6.65 (m, 4H), 6.63 (s, 1H), 5.37 (broad s, 1H), 3.37 (dd, 1H, J=11.1, 7.5 Hz), 3.30-3.10 (m, 5H), 2.95-2.75 (m, 4H), 2.73-2.65 (m, 1H), 2.58 (dd, 1H). LRMS (ES)+: 292.3 (M+H)+.

Workup

  1. customafter HPLC purification (C18
  2. washphase column, elution with a H2O/CH3CN gradient with 0.5% TFA)
  3. extractionextracted with chloroform
  4. washwashed with brine
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated to the title compound of EXAMPLE 116 as the free base

Sources & evidence

ORD record
ord-e3230b21a35241b0ba1bc5dac13a36c8
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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