2-chloro-N,N-dimethylacetamide → HCID 58529760, compound

HRID 1973012Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][C:7]([C:11]1[CH:12]=[C:13]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:14]3[C:19]=1[C:18]([NH2:20])=[N:17][CH:16]=[N:15]3)=[CH:6]2.ClC[C:36]([N:38]([CH3:40])[CH3:39])=[O:37]>>[NH2:20][C:18]1[C:19]2=[C:11]([C:7]3[CH:8]=[CH:9][C:10]4[C:5]([CH:6]=3)=[N:4][N:3]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:2]=4[NH2:1])[CH:12]=[C:13]([CH:21]3[CH2:26][CH2:25][N:24]([C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[CH2:23][CH2:22]3)[N:14]2[N:15]=[CH:16][N:17]=1

Participants

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamide

HCID 58529681HCID 58529681, compound

Product 1

HCID 58529760HCID 58529760, compoundYield 46%

Procedure

In a manner similar to the procedure described for Example 369 and using 5-(3-amino-2-benzyl-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, 40 mg (46%) of the desired product was isolated. 1H NMR (400 MHz, CD3OD) 8 ppm 7.82 (s, 1 H) 7.71 (d, 1 H) 7.23-7.37 (m, 6 H) 6.96 (d, 1 H) 6.57 (s, 1 H) 5.44 (s, 2 H) 3.79 (d, 2 H) 3.41 (dt, 1 H) 3.01 (d, 2 H) 2.86 (s, 6 H) 2.16 (d, 2 H) 1.77 (dt, 2 H). LC-MS [M+H]+=510.2, RT=2.21 min.

Sources & evidence

ORD record: ord-30aa70c30664448d84cbefccd723a58c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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