2-chloro-N,N-dimethylacetamide → HCID 71134087, compound

HRID 1972845Notes

Reaction equation

HRID 1972845 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>>[NH2:26][C:24]1[C:25]2=[C:17]([C:12]3[CH:13]=[CH:14][C:15]4[C:10]([CH:11]=3)=[N:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:16]=4)[CH:18]=[C:19]([CH:27]3[CH2:31][CH2:30][N:29]([CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[CH2:28]3)[N:20]2[N:21]=[CH:22][N:23]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 58529326HCID 58529326, compound

Product 1

HCID 71134087HCID 71134087, compoundYield 46.4%

Procedure

5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (100 mg, 0.244 mmol) was reacted with 2-chloro-N,N-dimethylacetamide (33 mg, 0.269 mmol) following the procedure of Example 136. The product was then chromatographed using 0-6% (2N NH3 in methanol)/dichloromethane to yield 56 mg (46%) of product. 1H NMR (300 MHz, dichloromethane-d2) δ 8.04 (s, 1 H), 7.89 (s, 1 H), 7.80 (d 1 H), 7.77-7.73 (m, 2 H), 7.36 (m, 5 H), 7.23 (d, 1 H), 6.66 (s, 1 H), 5.62 (s, 2 H), 5.43 (bs, 2 H), 4.00 (m, 1 H), 3.45 (m, 1 H), 3.35 (t, 1H), 3.18 (s, 2 H) 2.75-26.60 (m, 8 H), 2.45 (m, 1 H), 2.00 (m, 1 H); ES-MS m/z 495.2 [M+H]+, HPLC RT (min) 2.13.

Workup

  1. customThe product was then chromatographed

Sources & evidence

ORD record
ord-4c36a03dcce042969cfe44fd343d2c38
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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