Acetyl chloride → HCID 71134438, compound

HRID 1973000Notes

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.[C:33](Cl)(=[O:35])[CH3:34]>>[C:33]([N:14]1[CH2:15][CH2:16][CH:11]([C:10]2[N:6]3[C:7]([C:2]([NH2:1])=[N:3][CH:4]=[N:5]3)=[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]=2)[CH2:12][CH2:13]1)(=[O:35])[CH3:34]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 69303211HCID 69303211, compound

Product 1

HCID 71134438HCID 71134438, compoundYield 26%

Procedure

In a manner similar to the procedure described for the preparation of Example 331 and using 3-(4-amino-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl)-N-benzylbenzamide and acetyl chloride as starting material, 20 mg (26.0%) of the desired product was isolated. 1H NMR (400 MHz, CD3OD) δ 7.98 (s, 1H), 7.88-7.82 (m 2H), 7.62 (d, 1H), 7.55 (t, 1H), 7.36-7.28 (m, 4H), 7.25-7.20 (m, 1H), 6.58 (s, 1H), 4.67-4.59 (m, 3H), 4.06-3.98 (m, 1H), 3.52-3.43 (m, 1H), 3.33-3.24 (m, 1H), 2.78 (td, 1H), 2.20-2.08 (m, 5H), 1.73-1.63 (m, 2H); LC-MS m/z [M+H]+469.3, RT 2.34 min.

Workup

customIn a manner similar to the procedure described for the preparation of Example 331

Sources & evidence

ORD record: ord-3498cd28d6504dfb9a710967554e69a3
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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