Pyrrolidine → HCID 58529344, compound

HRID 1972879Notes

Reaction equation

CS(O[CH2:6][CH:7]1[CH2:9][CH:8]1[CH2:10][C:11]1[N:19]2[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]2)=[C:13]([C:21]2[CH:22]=[CH:23][C:24]3[C:28]([CH:29]=2)=[N:27][N:26]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:25]=3)[CH:12]=1)(=O)=O.[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:30]([N:26]1[CH:25]=[C:24]2[C:28]([CH:29]=[C:21]([C:13]3[CH:12]=[C:11]([CH2:10][CH:8]4[CH2:9][CH:7]4[CH2:6][N:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)[N:19]4[C:14]=3[C:15]([NH2:20])=[N:16][CH:17]=[N:18]4)[CH:22]=[CH:23]2)=[N:27]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (2-{[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]methyl}cyclopropyl)methyl methanesulfonate (0.2 g, 0.4 mmol) in DMF (2 mL) was added pyrrolidine (84 mg, 1.2 mmol) and DIEA (102 mg, 0.8 mmol), and the mixture was heated to 80° C. for 3 hours. The mixture was concentrated in vacuo and the residue was dissolved in methanol and purified by preparative HPLC to provide 11 mg (6%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.60 (s, 1 H), 8.05 (d, 2 H), 8.0 (s, 1 H), 7.90 (d, 1 H), 7.70 (s, 1 H), 7.60-7.40 (m, 7 H), 7.25 (d, 1 H), 720 (s, 1 H), 5.70 (s, 2 H), 2.9-2.8 (m, 2 H), 2.4-2.2 (m, 6 H), 1.7 (m, 4 H), 1.1-0.9 (m, 2 H), 0.5-0.4 (m, 2 H); ES-MS m/z 478.2 [M+H]P, HPLC RT (min) 2.29.

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthe residue was dissolved in methanol
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-7029a4a35cfc47d2894a9cf4e5bc3938
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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