(1R)-2,2-dimethylcyclopentan-1-amine → (R)-Ethyl 3-carbamoyl-4-((2,2-dimethylcyclopentyl)amino)pyrrolo[1,2-b]pyridazine-6-carboxylate

HRID 1408920Notes

Reaction equation

HRID 1408920 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:7].[C:9]([C:12]1[CH:17]=[N:16][N:15]2[CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:20]=[C:14]2[C:13]=1Cl)(=[O:11])[NH2:10].ClC1C2N(C=C(Cl)C=2)N=CC=1C(N)=O>>[C:9]([C:12]1[CH:17]=[N:16][N:15]2[CH:18]=[C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:20]=[C:14]2[C:13]=1[NH:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][C:2]1([CH3:8])[CH3:1])(=[O:11])[NH2:10]

Participants

4

Reactant 3

HCID 15196533(1R)-2,2-dimethylcyclopentan-1-amineHCID 68290691Ethyl 3-carbamoyl-4-chloropyrrolo[1,2-b]pyridazine-6-carboxylateHCID 682915404, 6-Dichloropyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68358891(R)-Ethyl 3-carbamoyl-4-((2,2-dimethylcyclopentyl)amino)pyrrolo[1,2-b]pyridazine-6-carboxylate

Procedure

Prepared by reacting (R)-2,2-dimethylcyclopentylamine with ethyl 3-carbamoyl-4-chloropyrrolo[1,2-b]pyridazine-6-carboxylate (Preparation 4) according to the procedure described in Step 5 of Intermediate 4. HPLC (condition B): retention time=3.67 min. LCMS (condition E): m/z 345+ve. 1H NMR (400 MHz, MeOD) δ ppm 10.86 (1 H, br. s.), 8.20 (1 H, s), 8.01 (1 H, d, J=1.76 Hz), 7.38 (1 H, d, J=1.54 Hz), 4.27-4.43 (2 H, m), 4.13-4.29 (1 H, m), 2.29-2.46 (1 H, m), 1.58-1.92 (5 H, m), 1.38 (3 H, t, J=7.15 Hz), 1.13 (3 H, s), 1.10 (3 H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-e84a504955824ac4b3d93caacde6fc97
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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