2-chloro-N-methylacetamide → HCID 58529549, compound

HRID 1972974Notes

Reaction equation

[NH2:1][C:2]1[N:3]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][C:7]([C:11]1[CH:12]=[C:13]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:14]3[C:19]=1[C:18]([NH2:20])=[N:17][CH:16]=[N:15]3)=[CH:6]2.Cl[CH2:34][C:35]([NH:37][CH3:38])=[O:36]>>[NH2:20][C:18]1[C:19]2=[C:11]([C:7]3[CH:8]=[CH:9][C:10]4[C:5]([CH:6]=3)=[N:4][N:3]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:2]=4[NH2:1])[CH:12]=[C:13]([CH:21]3[CH2:26][CH2:25][N:24]([CH2:34][C:35]([NH:37][CH3:38])=[O:36])[CH2:23][CH2:22]3)[N:14]2[N:15]=[CH:16][N:17]=1

Participants

Reactant 2

HCID 667732-chloro-N-methylacetamide

HCID 58529742HCID 58529742, compound

Product 1

HCID 58529549HCID 58529549, compoundYield 38%

Procedure

In a manner similar to the procedure described for the preparation of Example 298 and using 5-(3-amino-2-phenyl-2H-indazol-6-yl)-7-piperidin-4-yl-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine and 2-chloro-N-methylacetamide as starting materials, 42.3 mg (38%) of the desired product was isolated. 1H NMR (300 MHz, CD3OD) δ 7.81 to 7.78 (m, 2H), 7.70 to 7.67 (m, 2H), 7.61 (t, 2H), 7.53 to 7.49 (m, 1H), 7.35 (s, 1H), 6.95 (dd, 1H), 6.61 (s, 1H), 3.26 to 3.19 (m, 1H), 3.07 (s, 2H), 2.99 (d, 2H), 2.79 (s, 3H), 2.36 (t, 2H), 2.11 (d, 2H), 1.97 to 1.87 (m, 2H); ES-MS m/z 496.2 [M+H]+, RT (min) 1.25.

Workup

customIn a manner similar to the procedure described for the preparation of Example 298

Sources & evidence

ORD record: ord-37662735042d4a1eb0440481e41569f0
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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