Trifluoroacetic acid → HCID 58213481, compound

HRID 340379Notes

Reaction equation

HRID 340379 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:4]=2[N:3]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(O)(C(F)(F)F)=O>>[CH3:26][C:24]1[CH:23]=[CH:22][C:5]2=[C:6]3[C:11](=[C:2]([NH2:1])[N:3]=[C:4]2[CH:25]=1)[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:20][CH:21]=1)=[CH:7]3

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 86652362HCID 86652362, compound

Product 1

HCID 58213481HCID 58213481, compound

Procedure

8-Methyl-2-(4-(pyrrolidin-1-ylmethyl)phenethyl)benzo[f][1,7]naphthyridin-5-amine was prepared from 4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)benzaldehyde (from Example 172/Step 1) and pyrrolidine following the procedures described for Example 172, step 2. 1H NMR (Acetone-d6) TFA Salt: δ 8.88 (s, 1H), 8.82 (s, 1H), 8.82 (s, 1H), 8.43 (d, 1H), 8.38 (d, 1H), 7.58 (s, 1H), 7.51 (m, 1H), 7.33 (d, 2H), 4.16 (s, 2H), 3.32-3.38 (m, 4H), 2.55 (s, 3H), 2.20-2.32 (m, 4H), 1.90-1.99 (m, 4H). LRMS [M+H]=397.2

Sources & evidence

ORD record
ord-85235ef06ad74cc8a7e9c69c3f5ec8bf
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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