Acetyl chloride → HCID 58529528, compound

HRID 1972988Notes

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.[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: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]=2)[CH2:28][CH2:29]1)(=[O:35])[CH3:34]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 58529902HCID 58529902, compound

Product 1

HCID 58529528HCID 58529528, compoundYield 32%

Procedure

In a manner similar to the procedure described for the preparation of Example 331 and using 5-(2-benzyl-1,3-benzothiazol-5-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and acetyl chloride as starting material, 17.5 mg (32%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.06 (s, 1H), 7.95 (2H), 7.92 (s, 1H), 7.48 (d, 1H), 7.43-7.36 (m, 5H), 6.56 (s, 1H), 5.60 (s, 2H), 4.75-4.69 (m, 1H), 4.47 (s, 2H), 3.98-3.92 (m, 1H), 3.54-3.46 (m, 1H), 3.31-3.28 (m, 1H), 2.80-2.72 (m, 1H), 2.24-2.20 (m, 2H), 2.10 (s, 3H), 1.75-1.64 (m, 2H); LC-MS m/z [M+H]+ 483.2, RT 3.02 min.

Workup

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

Sources & evidence

ORD record: ord-f361736f8bdd483eaa5d411a6dd9b622
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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