Chloride → HCID 58529298, compound

HRID 1973016Notes

Reaction equation

HRID 1973016 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:15]3[C:10]([C:11]([NH2:16])=[N:12][CH:13]=[N:14]3)=[C:9]([C:17]3[CH:18]=[CH:19][C:20]4[C:24]([CH:25]=3)=[N:23][N:22]([CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:21]=4)[CH:8]=2)[CH2:3][CH2:2]1.[Cl-].ClC[C:36]([N:38]([CH3:40])[CH3:39])=[O:37]>>[NH2:16][C:11]1[C:10]2=[C:9]([C:17]3[CH:18]=[CH:19][C:20]4[C:24]([CH:25]=3)=[N:23][N:22]([CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:21]=4)[CH:8]=[C:7]([CH:4]3[CH2:3][CH2:2][N:1]([C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[CH2:6][CH2:5]3)[N:15]2[N:14]=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 312ChlorideHCID 758862-chloro-N,N-dimethylacetamideHCID 58529301HCID 58529301, compound

Product 1

HCID 58529298HCID 58529298, compoundYield 65%

Procedure

In a manner similar to the procedure described for Example 369 and using 7-piperidin-4-yl-5-[2-(pyridin-3-ylmethyl)-2H-indazol-6-yl]pyrrolo[2,1-f][1,2,4]triazin-4-amine and substituting dimethylcarbamyll chloride for 2-chloro-N,N-dimethylacetamide as starting material, 50 mg (65%) of the desired product was isolated. 1H NMR (400 MHz, CD3OD) δ 8.57 (s, 1 H) 8.49 (d, 1 H) 8.43 (s, 1 H) 7.75-7.80 (m, 3 H) 7.63 (s, 1 H) 7.42 (dd, 1 H) 7.21 (d, 1 H) 6.56 (s, 1 H) 5.71 (s, 2 H) 3.76 (d, 2 H) 3.34 (m, 1 H) 2.94 (dd, 2 H) 2.84 (s, 6 H) 2.06 (dd, 2 H) 1.73 (dt, 2 H). LC-MS [M+H]+=496.4, RT=1.08 min.

Sources & evidence

ORD record
ord-6e45f961d6d74c02991c543beaaea2db
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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