Dimethylformamide → HCID 58529701, compound

HRID 1972913Notes

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]4CCN[CH2:29][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(N(CC)C(C)C)(C)C.C[N:50]([CH:52]=O)[CH3:51]>>[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[CH2:28][CH2:29][CH2:52][N:50]([CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:51]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 758862-chloro-N,N-dimethylacetamide

HCID 81531Diisopropylethylamine

HCID 16066662HCID 16066662, compound

Product 1

HCID 58529701HCID 58529701, compoundYield 19%

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-(2-benzyl-2H-indazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (100 mg, 0.24 mmol) in DMF (1.5 mL) was added 2-chloro-N,N-dimethylacetamide (32 mg, 0.26 mmol) and N,N-diisopropylethylamine (123 μL, 0.71 mmol). The reaction was stirred at 60° C. for 17 h. The crude mixture was purified via ISCO® chromatography using 9:1 CH2Cl2 to afford 23 mg (19%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 8.54 (s, 1 H), 7.89 (s, 1 H), 7.78 (d, 1 H), 7.57 (s, 1 H), 7.25-7.45 (m, 5 H), 7.09-7.19 (m, 1 H), 6.63 (s, 1 H), 5.65 (s, 2 H), 3.34-3.52 (m, 2 H), 2.97-3.16 (m, 6H), 2.72-2.91 (m, 4 H), 2.09-2.43 (m, 2 H), 1.85-2.06 (m, 1 H), 1.44-1.89 (m, 2 H); ES-MS m/z 509.30 HPLC RT (min) 2.42.

Workup

customThe crude mixture was purified via ISCO® chromatography

Sources & evidence

ORD record: ord-100ccd86ec5a41fd84b5ee3a8371828e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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