N,N-Dimethylglycine → HCID 71134241, compound

HRID 1972999Notes

Reaction equation

HRID 1972999 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:17]3[CH:18]=[C:19]([CH:29]=[CH:30][CH:31]=3)[C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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.[CH3:32][N:33]([CH3:38])[CH2:34][C:35](O)=[O:36]>>[NH2:1][C:2]1[C:7]2=[C:8]([C:17]3[CH:18]=[C:19]([CH:29]=[CH:30][CH:31]=3)[C:20]([NH:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:21])[CH:9]=[C:10]([CH:11]3[CH2:12][CH2:13][N:14]([C:35](=[O:36])[CH2:34][N:33]([CH3:38])[CH3:32])[CH2:15][CH2:16]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 673N,N-DimethylglycineHCID 69337690HCID 69337690, compound

Product 1

HCID 71134241HCID 71134241, compoundYield 18%

Procedure

In a manner similar to the procedure described for the preparation of Example 342 using 3-(4-amino-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl)-N-phenylbenzamide and N,N dimethylglycine as starting material, 10 mg (18%) of the desired product was isolated. 1H NMR (400 MHz, DMSO-d6) δ10.24 (s, 1H), 8.02 (s, 1H), 7.96 (m, 2H), 7.80-7.76 (m, 2H), 7.64-7.58 (m, 2H), 7.38-7.36 (m, 2H), 7.11-7.09 (m, 1H), 6.64 (s, 1H), 4.52-4.44 (m, 1H), 4.10-4.00 (m, 1H), 3.50-3.38 (m, 1H), 3.37 (s, 2H), 3.22-3.16 (m, 1H), 2.80-2.70 (m, 1H), 2.36 (s, 6H), 2.10-2.04 (m, 2H), 1.78-1.61 (m, 1H), 1.59-1.30 (m, 1H); LC-MS m/z [M+H]+, 498.4, RT 2.11 min.

Sources & evidence

ORD record
ord-c678fbc55b8d4863a6a8c2f930e31c45
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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