Potassium Carbonate → HCID 21883103, compound

HRID 722244Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[C:20]([CH2:21][N:22]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][NH:18][C:4]=2[N:5]=[C:6]([NH:8]C(=O)CCCCCCC)[N:7]=1.Cl[CH2:38][C:39]1[C:44]([CH3:45])=[C:43]([O:46][CH3:47])[C:42]([CH3:48])=[CH:41][N:40]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:20]([CH2:21][N:22]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:19][N:18]([CH2:38][C:39]3[C:44]([CH3:45])=[C:43]([O:46][CH3:47])[C:42]([CH3:48])=[CH:41][N:40]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A suspension of octanoic acid {4-chloro-5-[(dibenzylamino)-methyl]-7H-pyrrolo[2,3-d]pyrimidin-2-yl}-amide (150 mg, 0.30 mmol), 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine (56 mg, 0.30 mmol) and K2CO3 (84 mg, 0.60 mmol) in dry DMF (1 mL) was heated to 45° C. overnight. After work-up (EtOAc) and evaporation, the residue was taken up in methanolic 4N HCl (1 mL), stirred at room temperature for 1 h, and neutralized to pH 7 with 2N NaOH. Extraction with EtOAc (10 mL×3), evaporation and purification by preparative TLC (MeOH/CH2Cl2 10:1) gave the title compound (70.5 mg, 45%). HPLC Rt: 5.362 min. 1H-NMR (DMSO-d6): δ 8.05 (s, 1H), 7.30–7.22 (m, 10H), 6.99(s, 1H), 6.57 (s, 2H), 5.27 (s 2H), 3.70 (s, 2H), 3.65 (s, 3H), 3.54 (s, 4H), 2.17 (s, 3H), 2.15 (s, 3H).

Workup

customAfter work-up (EtOAc) and evaporation
extractionExtraction
customwith EtOAc (10 mL×3), evaporation and purification by preparative TLC (MeOH/CH2Cl2 10:1)

Sources & evidence

ORD record: ord-364b3226e70c4549b5bb909d5d163cb5
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138402B2

Reaction notes

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