N,N-Dimethylglycine → HCID 58529790, compound

HRID 1972996Notes

Reaction equation

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

Participants

Reactant 2

HCID 673N,N-Dimethylglycine

HCID 58529699HCID 58529699, compound

Product 1

HCID 58529790HCID 58529790, compoundYield 24%

Procedure

In a manner similar to the procedure described for the preparation of Example 342 and using 5-(3-benzyloxyphenyl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and N,N-dimethylglycine as starting material, 20 mg (24%) of the desired product was isolated. 1H NMR (400 MHz, DMSO-d6) δ 7.90 (s, 1H), 7.45-7.30 (m, 6H), 7.10 (s, 1H), 7.05-6.97 (m, 2H), 6.56 (s, 1H), 5.13 (s, 2H), 4.48-4.42 (m, 1H), 4.18-4.12 (m, 1H), 3.41-3.32 (m, 3H), 3.20-3.10 (m, 2H), 3.05-2.97 (m, 1H), 2.76-2.68 (m, 1H), 2.16 (s, 6H), 2.06-1.98 (m, 2H); LC-MS m/z [M+H]+ 485.3, RT 2.32 min.

Workup

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

Sources & evidence

ORD record: ord-e8d09ebb4b914de78789b439f3456cd5
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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