2-chloro-N,N-dimethylacetamide → HCID 58529465, compound

HRID 1973017Notes

Reaction equation

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

Participants

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamide

HCID 58529425HCID 58529425, compound

Product 1

HCID 58529465HCID 58529465, compoundYield 83%

Procedure

In a manner similar to the procedure described for Example 369 and using 7 7-piperidin-4-yl-5-[2-(pyridin-2-ylmethyl)-2H-indazol-6-yl]pyrrolo[2,1-f][1,2,4]triazin-4-amine and substituting acetyl chloride for 2-chloro-N,N-dimethylacetamide as starting materials, 43 mg (83%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.58 (d, 1 H) 8.41 (s, 1 H) 7.65-7.81 (m, 3 H) 7.39 (s, 1 H) 7.19-7.26 (m, 3 H) 6.57 (s, 1 H) 5.78 (s, 2 H) 4.68 (d, 1 H) 4.02 (d, 1 H) 3.21-3.41 (m, 2 H) 2.76 (dd, 1 H) 2.01-2.19 (m, 5 H) 1.87 (dt, 2 H) LC-MS [M+H]+=467.4, RT=2.07 min.

Sources & evidence

ORD record: ord-b1f13809821b4cc5b0067d05005ffa71
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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