2-chloro-N,N-dimethylacetamide → HCID 58529411, compound

HRID 1972997Notes

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

Participants

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamide

HCID 58529699HCID 58529699, compound

Product 1

HCID 58529411HCID 58529411, compoundYield 23.6%

Procedure

In a manner similar to the procedure described for the preparation of Example 355 and using 5-(3-benzyloxyphenyl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and 2-chloro-N,N-dimethylacetamide as starting material, 20 mg (23.6%) of the desired product was isolated. 1H NMR (400 MHz, DMSO-d5) δ 7.90 (s, 1H), 7.44-7.32 (m, 6H), 7.10 (s, 1H), 7.02-6.98 (m, 2H), 6.59 (s, 1H), 5.16 (s, 2H), 3.16 (s, 2H), 3.15-3.04 (m, 1H), 3.03 (s, 3H), 2.97-2.90 (m, 2H), 2.80 (s, 3H), 2.22-2.14 (m, 2H), 1.98-1.92 (m, 2H), 1.74-1.64 (m, 2H); LC-MS m/z [M+H]+485.2, RT 2.29 min.

Workup

customIn a manner similar to the procedure described for the preparation of Example 355

Sources & evidence

ORD record: ord-56477a3dd8794615bf8e5b63fe3f62c0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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