2-Fluorobenzoic acid → HCID 57960981, compound

HRID 449047Notes

Reaction equation

HRID 449047 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.[F:29]C1C=CC=CC=1C(O)=O>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:25]3[CH2:26][CH2:27][CH2:28]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][C:20]=3[F:29])=[O:18])[CH2:15][CH:16]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 99352-Fluorobenzoic acidHCID 57960889HCID 57960889, compound

Product 1

HCID 57960981HCID 57960981, 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 2-fluorobenzoic acid. 1H NMR (400 MHz, CDCl3): δ=2.03 (ddd, J=11.75, 8.84, 3.16 Hz, 1H) 2.16 (ddd, J=14.46, 9.03, 5.56 Hz, 1H) 2.41-2.63 (m, 4H) 2.78 (br. s., 1H) 2.88 (br. s., 1H) 3.64 (t, J=5.05 Hz, 1H) 3.76 (quin, J=8.59 Hz, 1H) 4.11 (t, J=5.81 Hz, 2H) 4.51 (d, J=2.53 Hz, 1H) 5.82-6.12 (m, 1H) 6.64 (br. s., 2H) 6.87-6.98 (m, 1H) 7.04 (dd, J=5.31, 1.77 Hz, 1H) 7.15 (td, J=8.91, 3.66 Hz, 1H) 7.20-7.25 (m, 0H) 7.41-7.50 (m, 2H). MS (ES+): m/z 391.96 (100) [MH+]. HPLC: tR=2.16 min (OpenLynx polar—5 min).

Workup

  1. customPrepared
  2. customHPLC: tR=2.16 min (OpenLynx polar—5 min)

Sources & evidence

ORD record
ord-a7d0c2cd53b44fc4a6ab1c69c661b908
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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