N,N-Dimethylglycine → HCID 71134683, compound

HRID 1973001Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[C:8]([C:17]3[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=3)[C:20]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[CH3:33][N:34]([CH3:39])[CH2:35][C:36](O)=[O:37]>>[NH2:1][C:2]1[C:7]2=[C:8]([C:17]3[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=3)[C:20]([NH:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:36](=[O:37])[CH2:35][N:34]([CH3:39])[CH3:33])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 673N,N-Dimethylglycine

HCID 69303211HCID 69303211, compound

Product 1

HCID 71134683HCID 71134683, compoundYield 18%

Procedure

In a manner similar to the procedure described for the preparation of Example 342 and using 3-(4-amino-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl)-N-benzylbenzamide and N,N-dimethylglycine as starting material, 10 mg (18%) of the desired product was isolated. 1H NMR (400 MHz, CO3OD) δ 7.98 (s, 1H), 7.85 (d, 1H), 7.82 (s, 1H), 7.62 (d, 1H), 7.55 (t, 1H), 7.36-7.28 (m, 4H), 7.25-7.20 (m, 1H), 6.57 (s, 1H), 4.62-4.57 (m, 3H), 4.18-4.14 (m, 1H), 3.51-3.42 (m, 1H), 3.31-3.16 (m, 5H), 2.82-2.78 (m, 1H), 2.29 (s, 6H), 2.19-2.11 (m, 2H), 1.78-1.59 (m, 2H); 512.3, LC-MS m/z [M+H]+ 512.3, RT 1.96 min.

Workup

customIn a manner similar to the procedure described for the preparation of Example 342

Sources & evidence

ORD record: ord-c997ce3e5d924e48aaed00c925e4dbf0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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