2-chloro-N,N-dimethylacetamide → HCID 58529575, compound

HRID 1973014Notes

Reaction equation

HRID 1973014 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.ClC[C:36]([N:38]([CH3:40])[CH3:39])=[O:37]>>[NH2:25][C:23]1[C:24]2=[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]=[C:18]([CH:26]3[CH2:27][CH2:28][N:29]([C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[CH2:30][CH2:31]3)[N:19]2[N:20]=[CH:21][N:22]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 58529289HCID 58529289, compound

Product 1

HCID 58529575HCID 58529575, compoundYield 49%

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 dimethycarbamyl chloride for 2-chloro-N,N-dimethylacetamide as starting materials, 20 mg (49%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.05 (s, 1 H) 7.89 (s, 1 H) 7.78 (d, 1 H) 7.74 (s, 1 H) 7.33-7.39 (m, 2 H) 7.24 (dd, 1 H) 7.10 (ddd, 2 H) 6.59 (s, 1 H) 5.61 (s, 2 H) 3.79 (d, 2 H) 3.38-3.47 (m, 1 H) 2.97 (td, 2 H) 2.84 (s, 6 H) 2.17 (d, 1 H) 2.14 (s, 1 H) 1.76-1.71 (m, 2 H). LC-MS [M+H]+=513.1, RT=2.57 min.

Sources & evidence

ORD record
ord-cc8d2d8aeeb94c8cacfc61a9dc9f4af0
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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