1-Isoquinolinamine → N-[5-(2,4-dichlorophenyl)-3,6-dimethylpyrazin-2-yl]isoquinolin-1-amine

HRID 1824062Notes

Reaction equation

C(C1C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC(CC)=CN=1)C.Br[C:23]1[C:28]([CH3:29])=[N:27][C:26]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])=[C:25]([CH3:38])[N:24]=1.[C:39]1([NH2:49])[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][N:40]=1>>[Cl:37][C:31]1[CH:32]=[C:33]([Cl:36])[CH:34]=[CH:35][C:30]=1[C:26]1[N:27]=[C:28]([CH3:29])[C:23]([NH:49][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH:42]=[CH:41][N:40]=2)=[N:24][C:25]=1[CH3:38]

Participants

Reactant 3

HCID 737421-Isoquinolinamine

HCID 221474252-Bromo-5-(2,4-dichlorophenyl)-3,6-dimethylpyrazine

HCID 58583341(1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 22147487N-[5-(2,4-dichlorophenyl)-3,6-dimethylpyrazin-2-yl]isoquinolin-1-amine

Procedure

Following the procedure for the preparation of (1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol but substituting 2-bromo-5-(2,4-dichlorophenyl)-3,6-dimethylpyrazine and isoquinolin-1-amine, and making non-critical variations provided the title compound as a oil: 1H NMR (CDCl3) δ 2.36, 2.93, 6.75, 7.38, 7.53, 7.57, 8.96; HRMS (ESI+) calcd for C21H16Cl2N4 (M+H)+ 395.0830, found 395.0821.

Sources & evidence

ORD record: ord-a1e0c59aa484433597b859b1d7a1977d
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041672B2

Reaction notes

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