3-Bromopyridine → (7Br,11as)-n-(3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4h-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-amine

HRID 23271

Reaction equation

HRID 23271 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:8][C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([CH2:18][O:19][CH2:20][CH2:21][N:14]3[C@H:13]3[CH2:22][CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25][C@@H:12]23)[CH:17]=1.[OH-].[NH4+]>>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:8][C:9]2[CH:10]=[C:11]3[C:15]4=[C:16]([CH2:18][O:19][CH2:20][CH2:21][N:14]4[C@H:13]4[CH2:22][CH2:23][NH:24][CH2:25][C@@H:12]34)[CH:17]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 122863-BromopyridineHCID 14923Ammonium HydroxideHCID 86586438Tert-butyl (7br,11as)-6-amino-1,2,7b,10,11,11a-hexahydro-4h-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8h)carboxylate

Product 1

HCID 60071799(7Br,11as)-n-(3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4h-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-amine

Procedure

Using 3-bromopyridine and following the procedures described in EXAMPLE 56, Part C, tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate from EXAMPLE 56, Part B was converted into (7bR,11aS)-N-(3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indol-6-amine, bis-trifluoroacetic acid salt. This material was free-based with aq ammonium hydroxide, extracted with chloroform, washed with brine, dried (K2CO3) and concentrated to afford the title compound of EXAMPLE 115. LRMS (ES)+: 323.4 (M+H)+.

Workup

  1. extractionextracted with chloroform
  2. washwashed with brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dcd5e410c4e64b6bbbf967725f5dcb93
Source dataset
uspto-grants-2005_02
Patent number
US06849619B2

Linked notes

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