2-chloro-N,N-dimethylacetamide → HCID 58529375, compound

HRID 1973003Notes

Reaction equation

HRID 1973003 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[CH2:32][CH2:31][NH:30][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.C(N(CC)C(C)C)(C)C.Cl[CH2:43][C:44]([N:46]([CH3:48])[CH3:47])=[O:45]>>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=4)[CH:18]=[C:19]([CH:27]3[CH2:32][CH2:31][N:30]([CH2:43][C:44]([N:46]([CH3:48])[CH3:47])=[O:45])[CH2:29][CH2:28]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

4

Reactant 3

HCID 758862-chloro-N,N-dimethylacetamideHCID 81531DiisopropylethylamineHCID 16066662HCID 16066662, compound

Product 1

HCID 58529375HCID 58529375, compoundYield 52.1%

Conditions

Temperature
60 °C

Procedure

The suspension of 5-(2-benzyl-2H-indazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (500 mg, 1.81 mmol) was treated with N,N-diisopropylethylamine (411 uL, 2.36 mmol) followed by 2-chloro-N,N-dimethylacetamide (192 uL, 1.42 mmol). The mixture was heated at 60° C. for 3 h then cooled to rt. The white solid was filtered then purified by ISCO® using 0-10% 2N NH3 in MeOH/EtOAc. 313 mg (52.1%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.42 (s, 1H), 8.04 (s, 1H), 8.19-8.12 (m, 2H), 7.82-7.70 (m, 5H), 7.62-7.60 (d, 1H), 6.99 (s, 1H), 6.02 (s, 2H), 5.96 (s, 2H), 3.70-3.59 (m, 3H), 3.50 (s, 3H), 3.48-3.40 (m, 2H), 3.36 (s, 3H), 2.79-2.50 (m, 2H), 2.59-2.48 (m, 2H), 2.36-2.24 (m, 2H); LC-MS m/z[M+H]+ 509.2, RT 2.09 min.

Workup

  1. temperaturethen cooled to rt
  2. filtrationThe white solid was filtered
  3. customthen purified by ISCO®

Sources & evidence

ORD record
ord-91afc99afd5245aa85f46ee8a6c0f289
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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