1-Bromo-2,4-dichlorobenzene → HCID 60088419, compound

HRID 1836579Notes

Reaction equation

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

Participants

Reactant 2

HCID 709471-Bromo-2,4-dichlorobenzene

HCID 131724537HCID 131724537, compound

Product 1

HCID 60088419HCID 60088419, compound

Procedure

Using 2,4-dichlorobromobenzene and following the procedures described in EXAMPLE 72, (±)-trans tert-butyl 2-amino-5,6,8a,9,11,11a-hexahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline-10(8H)-carboxylate was converted into the title compound of EXAMPLE 75 as an off-white powder. 1H NMR (300 MHz, CDCl3) δ 1.25 (br s, 1H), 1.70-1.90 (br s, 1H), 1.90-2.20 (m, 2H), 2.70-2.80 (m, 4H), 2.91 (t, 1H, J=9.3 Hz), 3.30-3.60 (m, 5H), 3.54 (m, 1H), 5.78 (br s, 1H), 6.51 (s, 1H), 6.68 (s, 1H), 6.79 (d, 1H, J=8.0 Hz), 7.00 (d, 1H, J=8.0 Hz), 7.25 (s, 1H). LRMS (ES)+: 374 (M+H)+.

Sources & evidence

ORD record: ord-d1b5f97599454dea93919aedc5e91ecc
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777406B2

Reaction notes

Loading…