3-Bromo-5-chloropyridine-2-carbonitrile → HCID 131724730, compound

HRID 23297Notes

Reaction equation

Br[C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:11][C:12]1[CH:13]=[C:14]2[C:18]3=[C:19]([CH2:21][O:22][CH2:23][CH2:24][N:17]3[C@H:16]3[CH2:25][CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][C@@H:15]23)[CH:20]=1>>[ClH:8].[ClH:8].[Cl:8][C:6]1[CH:7]=[C:2]([NH:11][C:12]2[CH:13]=[C:14]3[C:18]4=[C:19]([CH2:21][O:22][CH2:23][CH2:24][N:17]4[C@H:16]4[CH2:25][CH2:26][NH:27][CH2:28][C@@H:15]34)[CH:20]=2)[C:3]([C:9]#[N:10])=[N:4][CH:5]=1

Participants

Reactant 2

HCID 225912463-Bromo-5-chloropyridine-2-carbonitrile

HCID 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 131724730HCID 131724730, compound

Procedure

Following the procedures described in Example 176 and using 3-bromo-5-chloro-2-cyanopyridine, 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 the title compound of Example 177. ESI MS m/z 382.3/384.3 [C20H20CIN5O+H]+.

Sources & evidence

ORD record: ord-ccc3b24ca0b6486588acb2b76709b7ed
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849619B2

Reaction notes

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