2-Chloro-3,5-dimethylpyrazine → HCID 25115828, compound

HRID 1099417Notes

Reaction equation

HRID 1099417 reaction equation
[CH2:1]([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2B2OC(C)(C)C(C)(C)O2)[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:36]1[C:41]([CH3:42])=[N:40][C:39]([CH3:43])=[CH:38][N:37]=1>>[CH2:28]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:36]2[C:41]([CH3:42])=[N:40][C:39]([CH3:43])=[CH:38][N:37]=2)[O:11][CH2:10]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 116726802-Chloro-3,5-dimethylpyrazineHCID 25114260(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine

Product 1

HCID 25115828HCID 25115828, compoundYield 72%

Procedure

The title compound was synthesized as described for Intermediate example I-28 in 72% yield starting from (S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine and 2-chloro-3,5-dimethylpyrazine (1.2 equiv); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (s, 1 H), 7.24-7.31 (m, 8 H), 7.17-7.22 (m, 2 H), 7.11-7.17 (m, 1 H), 6.82 (dd, 1 H), 6.74 (dd, 1 H), 4.27-4.34 (m, 1 H), 4.07 (t, 1 H), 3.56-3.67 (m, 4 H), 2.95-3.05 (m, 1 H), 2.56-2.67 (m, 1 H), 2.54 (s, 3 H), 2.28-2.40 (m, 1 H), 2.24 (s, 3 H); MS (APPI/APCI) m/z 436[M+H+].

Sources & evidence

ORD record
ord-91a568246161467dbcdc71c47c56a0f5
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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