1,1'-Carbonyldiimidazole → HCID 11844913, compound

HRID 1363135Notes

Reaction equation

HRID 1363135 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[N:13]1([C:22]2[N:27]=[C:26]([NH:28][C@H:29]3[C:38]4[C:33](=[C:34]([F:39])[CH:35]=[CH:36][CH:37]=4)[O:32][CH2:31][CH2:30]3)[C:25]([NH2:40])=[CH:24][N:23]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1>C1COCC1>[N:13]1([C:22]2[N:27]=[C:26]3[C:25]([NH:40][C:1](=[O:2])[N:28]3[C@H:29]3[C:38]4[C:33](=[C:34]([F:39])[CH:35]=[CH:36][CH:37]=4)[O:32][CH2:31][CH2:30]3)=[CH:24][N:23]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59846421HCID 59846421, compound

Product 1

HCID 11844913HCID 11844913, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (0.2 g) was added to a solution of the above amine in THF (10 mL). The resulting mixture was stirred at RT overnight, silica gel was added, then the solvents were removed under reduced pressure and purified via column chromatography, elution with 5% MeOH/DCM, to yield the titled product (28 mg), MH+=403, 1H NMR (CDCl3) δ 10.6 (s, 1H), 8.9 (s, 1H), 8.3 (s, 1H), 7.8 (m, 2H), 7.3 (m, 2H), 7.0 (m, 1H), 6.7 (m, 1H), 5.9 (dd, 1H), 4.7 (m, 1H), 4.4 (t, 1H), 2.7 (m, 1H), 2.3 (m, 1H) ppm, 19F NMR δ −135.7 (m). Chiral HPLC—no evidence of other enantiomer, Method; Chiralcel™ OD-H (0.46×25 cm analytical column, Daicel Chemical Industries) isocratic 15% (0.05% TFA/EtOH) 85% (0.05% TFA/Hex), Rt=19.5 min (R)-enantiomer, Rt=22.4 min (S)-enantiomer.

Workup

  1. additionsilica gel was added
  2. customthe solvents were removed under reduced pressure
  3. custompurified via column chromatography, elution with 5% MeOH/DCM

Sources & evidence

ORD record
ord-38b61a1aa7754912a65bcdb492c184b7
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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