Acetyl chloride → HCID 58529643, compound

HRID 1972994Notes

Reaction equation

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

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 58529821HCID 58529821, compound

Product 1

HCID 58529643HCID 58529643, compoundYield 26%

Procedure

In a manner similar to the procedure described for the preparation of Example 331 and using 5-[3-(benzyloxy)-5-fluorophenyl]-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and acetyl chloride as starting material, 20 mg (26%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 7.91 (s, 1H), 7.47-7.35 (m, 5H), 6.90 (s, 1H), 6.82 (d, 1H), 6.75 (d, 1H), 6.50 (s, 1H), 5.48 (s, 2H), 5.13 (s, 2H), 4.76-4.71 (m, 1H), 3.97-3.90 (m, 1H), 3.54-3.44 (m, 1H), 3.26 (td, 1H), 2.74 (td, 1H), 2.22-2.15 (m, 2H), 2.09 (s, 3H), 1.72-1.60 (m, 2H); LC-MS m/z[M+H]+ 460.4, RT 3.10 min.

Workup

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

Sources & evidence

ORD record: ord-33a4d55ab2d646c39d38e362652c2058
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

Loading…