2-chloro-N,N-dimethylacetamide → HCID 58529707, compound

HRID 1973019Notes

Reaction equation

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

Participants

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamide

HCID 58529635HCID 58529635, compound

Product 1

HCID 58529707HCID 58529707, compoundYield 16%

Procedure

In a manner similar to the procedure described for Example 369 and using 5-[2-(cyclohexylmethyl)-2H-indazol-6-yl]-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and substituting methane sulfonyl chloride for 2-chloro-N,N-dimethylacetamide as starting materials, 11 mg (16%) of the desired product was isolated. 1H NMR (400 MHz, CD3OD) δ 8.25 (s, 1 H) 7.79-7.84 (m, 2 H) 7.65 (s, 1 H) 7.23 (d, 1 H) 6.63 (s, 1 H) 4.29 (d, 2 H) 3.85 (d, 2 H) 3.35-3.40 (m, 1 H) 2.94 (td, 2 H) 2.88 (s, 3 H) 1.58-2.24 (m, 10 H) 1.07-1.30 (m, 5 H). LC-MS [M+H]+=508.3, RT=2.86 min.

Sources & evidence

ORD record: ord-020bb54dcde540bb9deda0e173b82926
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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