Acetyl chloride → 7-(1-Acetylpiperidin-4-yl)-5-(2-benzyl-1,3-benzothiazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1972984Notes

Reaction equation

HRID 1972984 reaction equation
[CH2:1]([C:8]1[S:9][C:10]2[CH:16]=[C:15]([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:14]=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](Cl)(=[O:35])[CH3:34]>>[C:33]([N:30]1[CH2:31][CH2:32][CH:27]([C:19]2[N:20]3[C:25]([C:24]([NH2:26])=[N:23][CH:22]=[N:21]3)=[C:17]([C:15]3[CH:14]=[CH:13][C:11]4[N:12]=[C:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[S:9][C:10]=4[CH:16]=3)[CH:18]=2)[CH2:28][CH2:29]1)(=[O:35])[CH3:34]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 585293605-(2-Benzyl-1,3-benzothiazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 585293107-(1-Acetylpiperidin-4-yl)-5-(2-benzyl-1,3-benzothiazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 54.8%

Procedure

In a manner similar to the procedure described for the preparation of Example 331 and using 5-(2-benzyl-1,3-benzothiazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and acetyl chloride as starting material, 27 mg (54.8%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.04 (d, 1H), 7.91 (s, 1H), 7.89 (s, 1H), 7.59 (d, 1H), 7.41-7.29 (m, 5H), 7.56 (s, 1H), 4.76-4.68 (m, 1H), 4.44 (s, 2H), 3.96-3.90 (m, 1H), 3.56-3.44 (m, 1H), 3.30-3.24 (m, 1H), 2.70-2.80 (m, 1H), 2.22-2.12 (m, 2H), 2.10 (s, 3H), 1.76-1.60 (m, 2H) LC-MS m/z [M+H]+ 483.3, RT 2.76 min.

Workup

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

Sources & evidence

ORD record
ord-c7f8331ca7ed4c4785ce91c352b22b4a
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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