6-Bromo-4-(3-hydroxy-2,2-dimethylcyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide → 6-Bromo-4-(2,2-dimethyl-3-oxocyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 1408944Notes

Reaction equation

HRID 1408944 reaction equation
CC1(C)C(=O)CCC1NC1C2N(C=CC=2)N=CC=1C(N)=O.[Br:22][C:23]1[CH:24]=[C:25]2[C:30]([NH:31][CH:32]3[CH2:36][CH2:35][CH:34]([OH:37])[C:33]3([CH3:39])[CH3:38])=[C:29]([C:40]([NH2:42])=[O:41])[CH:28]=[N:27][N:26]2[CH:43]=1>>[Br:22][C:23]1[CH:24]=[C:25]2[C:30]([NH:31][CH:32]3[CH2:36][CH2:35][C:34](=[O:37])[C:33]3([CH3:39])[CH3:38])=[C:29]([C:40]([NH2:42])=[O:41])[CH:28]=[N:27][N:26]2[CH:43]=1

Participants

3

Reactant 2

HCID 682910726-Bromo-4-(3-hydroxy-2,2-dimethylcyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamideHCID 683586194-[(2,2-Dimethyl-3-oxocyclopentyl)amino]pyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 682911676-Bromo-4-(2,2-dimethyl-3-oxocyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamideYield 81.4%

Procedure

Following conditions described in Step 1 of Intermediate 22, 6-bromo-4-(3-hydroxy-2,2-dimethylcyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (395 mg, 1.076 mmol, from Step 1) was converted to 6-bromo-4-(2,2-dimethyl-3-oxocyclopentylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (320 mg, 80% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 8.19 (1 H, s), 7.69 (1 H, d, J=1.76 Hz), 7.16 (1 H, d, J=1.76 Hz), 2.36-2.73 (3 H, m), 1.89-2.06 (1 H, m), 1.15 (6 H, s); MS (ES+) m/z: 365.2, 367.1 (M+H).

Sources & evidence

ORD record
ord-80e096c31a9844858895375f7159fdb4
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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