Potassium Iodide → HCID 58529355, compound

HRID 1972817Notes

Reaction equation

[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[O:32][CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[NH2:26][C:24]1[C:25]2=[C:17]([C:12]3[CH:13]=[CH:14][C:15]4[C:10]([CH:11]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:16]=4)[CH:18]=[C:19]([CH:27]3[O:32][CH2:31][CH2:30][N:29]([CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:28]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 5-(2-benzyl-2H-indazol-6-yl)-7-morpholin-2-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (247 mg, 0.521 mmol) in DMF (5 mL) was treated with 2-chloro-N,N-dimethylacetamide (115 mg, 0.94 mmol), potassium carbonate (658 mg, 4.8 mmol) and potassium iodide (19 mg, 0.12 mmol) and the mixture vigorously stirred at 60° C. for 18 h. Basic, aqueous workup and purification by column chromatography (CH2Cl2:MeOH:NH3) gave 312 mg (50%) of the desired compound. 1H NMR (300 MHz, DMSO-d6) δ 7.89 (s, 1 H), 7.76 (dd, 1 H, J=9, 1 Hz), 7.53 (s, 1H), 7.25 to 7.36 (m, 3H), 7.18-7.23 (m, 2H), 7.09 (d, 1 H, J=9 Hz), 6.60 (s, 1H), 5.63 (s, 2H), 3.14 (s, 2H), 3.03 (s, 3H), 2.89-2.94 (m, 2H), 2.80 (s, 3H), 2.62 (s, 3H), 2.12-2.24 (m, 2H), 1.93-2.03 (m, 2H), 1.63-1.79 (m, 2H); ES-MS m/z 523.2 [M+H]+, HPLC RT (min) 2.21.

Workup

customBasic, aqueous workup and purification by column chromatography (CH2Cl2:MeOH:NH3)

Sources & evidence

ORD record: ord-b113be0d88944babbbce14ffb1f2aca7
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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