2-chloro-N,N-dimethylacetamide → HCID 58529560, compound

HRID 1973013Notes

Reaction equation

[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[CH:15]=[C:14]3[C:9]([CH:10]=[C:11]([C:16]4[CH:17]=[C:18]([CH:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]5)[N:19]5[C:24]=4[C:23]([NH2:25])=[N:22][CH:21]=[N:20]5)[CH:12]=[CH:13]3)=[N:8]2)=[CH:4][CH:3]=1.Cl[CH2:35][C:36](N(C)C)=[O:37]>>[C:36]([N:29]1[CH2:28][CH2:27][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]=[CH:13][C:14]4[C:9]([CH:10]=3)=[N:8][N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:33][CH:32]=3)[CH:15]=4)[CH:17]=2)[CH2:31][CH2:30]1)(=[O:37])[CH3:35]

Participants

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamide

HCID 58529289HCID 58529289, compound

Product 1

HCID 58529560HCID 58529560, compoundYield 55%

Procedure

In a manner similar to the procedure described for Example 369 and using 5-[2-(4-fluorobenzyl)-2H-indazol-6-yl]-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine and substituting acetyl chloride for 2-chloro-N,N-dimethylacetamide as starting materials, 30 mg (55%) of the desired product was isolated. 1H NMR (400 MHz, CD3OD) δ 8.34 (s, 1 H) 7.81 (s, 1 H) 7.77 (d, 1 H) 7.62 (d, 1 H) 7.32-7.40 (m, 2 H) 7.19 (d, 1 H) 7.03-7.10 (m, 2 H) 6.55 (s, 1 H) 5.61 (s, 2 H) 4.63 (d, 1 H) 4.00 (d, 1 H) 3.45 (tt, 1 H) 3.25 (td, 1 H) 2.75 (td, 1 H) 2.07-2.18 (m, 5 H) 1.62-1.72 (m, 2 H).

Sources & evidence

ORD record: ord-9b7f451abc1a4c8daf0a311c09d21230
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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