2-chloro-N,N-dimethylacetamide → HCID 58529705, compound

HRID 1972990Notes

Reaction equation

[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36]>>[NH2:26][C:24]1[C:25]2=[C:17]([C:14]3[CH:15]=[CH:16][C:10]4[S:9][C:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[N:12][C:11]=4[CH:13]=3)[CH:18]=[C:19]([CH:27]3[CH2:32][CH2:31][N:30]([CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:29][CH2:28]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamide

HCID 58529902HCID 58529902, compound

Product 1

HCID 58529705HCID 58529705, compoundYield 36.2%

Procedure

In a manner similar to the procedure described for the preparation of Example 355 and using 5-(2-benzyl-1,3-benzothiazol-5-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and 2-chloro-N,N-dimethylacetamide as starting material, 21.6 mg (36.2%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.06 (s, 1H), 7.92 (d, 1H), 7.91 (s, 1H), 7.49 (d, 1H), 7.43-7.36 (m, 5H), 6.59 (s, 1H), 5.43 (s, 2H), 4.47 (s, 2H), 3.32-3.23 (m, 1H), 3.21 (s, 2H), 3.10 (s, 3H), 3.09-3.03 (m, 2H), 2.92 (s, 3H), 2.40-2.32 (m, 2H), 2.16-2.12 (m, 2H), 1.94-1.82 (m, 2H); LC-MS m/z[M+H]+ 526.2, RT 2.30 min.

Workup

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

Sources & evidence

ORD record: ord-acb5e63cca854329aec298bdaea81cef
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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