2-chloro-N,N-dimethylacetamide → HCID 58529416, compound

HRID 1972992Notes

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.Cl[CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>>[NH2:25][C:23]1[C:24]2=[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]=[C:18]([CH:26]3[CH2:31][CH2:30][N:29]([CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[CH2:28][CH2:27]3)[N:19]2[N:20]=[CH:21][N:22]=1

Participants

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamide

HCID 58529821HCID 58529821, compound

Product 1

HCID 58529416HCID 58529416, compoundYield 17%

Procedure

In a manner similar to the procedure described for the preparation of Example 355 and using 5-[3-(benzyloxy)-5-fluorophenyl]-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and 2-chloro-N,N-dimethylacetamide as starting material, 20 mg (17%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 7.89 (s, 1H), 7.47-7.36 (m, 5H), 6.89 (s, 1H), 6.82 (d, 1H), 6.74 (d, 1H), 6.52 (s, 1H), 5.56 (s, 2H), 5.13 (s, 2H), 3.25-3.20 (m, 1H), 3.18 (s, 2H), 3.10 (s, 3H), 3.02-2.98 (m, 2H), 2.92 (s, 3H), 2.26 (t, 2H), 2.11-2.08 (m, 2H), 1.82-1.78 (m, 2H); LC-MS m/z [M+H]+ 503.9, RT 2.77 min.

Workup

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

Sources & evidence

ORD record: ord-fa3f4e736fcc487c871269571b0e7d65
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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