1,3-Propanediamine → HCID 10194258, compound

HRID 646591Notes

Reaction equation

HRID 646591 reaction equation
C1(B(O)O)C=CC=CC=1.[CH3:10][N:11]([CH3:35])[C:12]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][C:15]([C:24]2[N:25]=[C:26](O)[C:27]3[CH:28]=[CH:29][CH:30]=[N:31][C:32]=3[CH:33]=2)=[CH:14][CH:13]=1.[NH2:36][CH2:37][CH2:38][CH2:39][NH2:40]>>[NH2:36][CH2:37][CH2:38][CH2:39][NH:40][C:26]1[N:25]=[C:24]([C:15]2[CH:16]=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]([N:11]([CH3:35])[CH3:10])=[CH:13][CH:14]=2)[CH:33]=[C:32]2[C:27]=1[CH:28]=[CH:29][CH:30]=[N:31]2

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 66827Phenylboronic AcidHCID 178482630HCID 178482630, compound

Product 1

HCID 10194258HCID 10194258, compound

Procedure

Treatment of the above intermediate with 2-methylnicotinic acid according to Method A (Example 1) provided the corresponding [1,6]napthyridin-5-ol. Treatment of this with phenylboronic acid using the procedure described in Example 5 provided 7-(6-dimethylamino-biphenyl-3-yl)-[1,6]naphthyridin-5-ol. Conversion to the 5-chloro intermediate using Method B, followed by treatment of this with 1,3-diaminopropane by the procedure described in Method C (Example 3) provided the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.82 (dd, 1H), 8.16 (d, 1H), 8.04 (dd, 1H), 8.00 (d, 1H), 7.63 (dd, 2H), 7.52 (s, 1H), 7.41 (t, 2H), 7.29 (t, 1H), 7.19 (dd, 1H), 7.08 (d, 1H), 3.84 (t, 2H), 3.00 (t, 2H), 2.58 (s, 6H), 1.99 (t, 2H); MS (m/e) calculated for C25H27N5 397, found 398.3 (M+H).

Sources & evidence

ORD record
ord-a5bf954348ae4017be816c5133e1e780
Source dataset
uspto-grants-2010_04
Patent number
US07705151B2

Reaction notes

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