HCID 66874895, compound → HCID 58213709, compound

HRID 340323Notes

Reaction equation

HRID 340323 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:25]=[CH:24][C:13]2=[C:14]3[C:19](=[C:20]([NH2:22])[N:21]=[C:12]2[CH:11]=1)[N:18]=[C:17](Cl)[CH:16]=[CH:15]3)(C(C)(C)C)(C)C.ClC1C(C#N)=NC=C([CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH3:44])=[CH:37][CH:36]=2)C=1>>[NH2:22][C:20]1[C:19]2[N:18]=[CH:17][C:16]([CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][CH3:44])=[CH:37][CH:36]=3)=[CH:15][C:14]=2[C:13]2[CH:24]=[CH:25][C:10]([CH2:9][OH:8])=[CH:11][C:12]=2[N:21]=1

Participants

3

Reactant 2

HCID 66874895HCID 66874895, compoundHCID 86652357HCID 86652357, compound

Product 1

HCID 58213709HCID 58213709, compound

Procedure

(5-Amino-2-(4-propoxyphenethyl)benzo[f][1,7]naphthyridin-8-yl)methanol was prepared from 8-((tert-butyldimethylsilyloxy)methyl)-3-chlorobenzo[f][1,7]naphthyridin-5-amine (from Example 99/step 1) and 3-chloro-5-(4-propoxyphenethyl)picolinonitrile (from Example 79/step 2) following the procedures described for Example 44/Step 4 and Example 99/step 3 (deprotection of TBS). 1H NMR (acetone-d6): δ 8.79 (d, 1H), 8.70 (d, 1H), 8.35 (d, 1H), 7.61 (d, 1H), 7.33 (dd, 1H), 7.17 (d, 2H), 6.83 (d, 2H), 6.57 (br s, 2H), 4.77 (d, 2H), 4.34 (t, 1H), 3.89 (t, 2H), 3.22 (t, 2H), 3.06 (t, 2H), 1.83-1.70 (m, 2H), 1.00 (t, 3H). LRMS [M+H]=388.2.

Sources & evidence

ORD record
ord-7ace2858c059484585cf527d5dadaef3
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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