2-chloro-N,N-dimethylacetamide → HCID 58529367, compound

HRID 1973020Notes

Reaction equation

HRID 1973020 reaction equation
[CH:1]1([CH2:7][N:8]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:17]4[CH:18]=[C:19]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[N:20]5[C:25]=4[C:24]([NH2:26])=[N:23][CH:22]=[N:21]5)[CH:13]=[CH:14]3)=[N:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC[C:35]([N:37]([CH3:39])[CH3:38])=[O:36]>>[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]([CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:16]=4)[CH:18]=[C:19]([CH:27]3[CH2:28][CH2:29][N:30]([C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:31][CH2:32]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 58529635HCID 58529635, compound

Product 1

HCID 58529367HCID 58529367, compoundYield 31%

Procedure

In a manner similar to the procedure described for Example 369 and using 5-[2-(cyclohexylmethyl)-2H-indazol-6-yl]-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and substituting dimethylcarbamyl chloride for 2-chloro-N,N-dimethylacetamide as starting materials, 21 mg (31%) of the desired product was isolated. 1H NMR (400 MHz, CD3OD) δ 8.25 (s, 1 H) 7.79-7.83 (m, 2 H) 7.65 (s, 1 H) 7.21 (d, 1 H) 6.60 (s, 1 H) 4.28 (d, 2 H) 3.83 (d, 2 H) 3.36-3.41 (m, 1 H) 2.97 (td, 2 H) 2.87 (s, 6 H) 1.99-2.16 (m, 3 H) 1.58-1.85 (m, 7 H) 1.04-1.27 (m, 5 H). LC-MS [M+H]+=501.6, RT=3.04 min.

Sources & evidence

ORD record
ord-dc92cd342309467c84a3805cfb0070e2
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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