3-Pyridinecarboxaldehyde → 4-[2-(4-{3-[(Pyridin-3-ylmethyl)-amino]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

HRID 14781Notes

Reaction equation

HRID 14781 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=1>>[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][NH:1][C:2]2[CH:3]=[C:4]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH2:15][CH2:16][C:17]4[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=4)[N:9]=3)[CH:5]=[CH:6][CH:7]=2)[CH:25]=1

Participants

3

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 670450394-{2-[4-(3-Amino-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Product 1

HCID 670448754-[2-(4-{3-[(Pyridin-3-ylmethyl)-amino]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

Procedure

Intermediate 24 was coupled with pyridine 3-carboxaldehyde following procedure E. LC-MS showed the product had the expected M+H+ of 398. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.6 (s, 1H), 8.4 (d, 1H) 8.2 (d, 1H) 7.8 (d, 1H), 7.4-7.3 (m, 3H), 7.2 (t, 1H), 7.1 (d, 2H), 6.9 (d, 2H), 6.8 (d, 1H), 6.7 (d, 1H), δ 4.4 (s, 2H), δ 3.6 (t, 2H), 2.8 (t, 2H).

Sources & evidence

ORD record
ord-e7f1bb08aa2047b88412c8df0527bd6c
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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