Cyclohexanecarboxylic acid → HCID 44539001, compound

HRID 449046Notes

Reaction equation

HRID 449046 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:25]3[CH2:28][CH2:27][CH2:26]3)=[N:9][C:10]=2[C:11]2[CH2:12][CH2:13][N:14]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[CH2:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1.C1(C(O)=O)CCCCC1>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:25]3[CH2:28][CH2:27][CH2:26]3)=[N:9][C:10]=2[C:11]2[CH2:12][CH2:13][N:14]([C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])[CH2:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 7413Cyclohexanecarboxylic acidHCID 57960889HCID 57960889, compound

Product 1

HCID 44539001HCID 44539001, compound

Procedure

Prepared according to a procedure analogous to that described for synthesis of [4-(8-amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-3,6-dihydro-2H-pyridin-1-yl]-phenylmethanone, except using cyclohexanecarboxylic acid. 1H NMR (400 MHz, CDCl3): δ=1.25-1.40 (m, 3H) 1.60 (br. s., 2H) 1.85 (dd, J=8.97, 2.65 Hz, 5H) 2.05 (dd, J=8.84, 3.28 Hz, 1H) 2.14-2.27 (m, 1H) 2.42-2.64 (m, 5H) 2.78 (br. s., 2H) 3.69-3.97 (m, 3H) 4.31 (br. s., 2H) 6.07 (br. s., 1H) 6.83 (br.s., 1H) 7.01 (d, J=5.05 Hz, 1H). MS (ES+): m/z 380.03 (100) [MH+]. HPLC: tR=2.27 min (ZQ3, polar—5 min).

Workup

  1. customPrepared
  2. custom5 min

Sources & evidence

ORD record
ord-cc9fa0e63bdb422aad1f04d32065e1f8
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…