2-Methylnicotinic acid → 1-Ethyl-3-(4-(7-(2-methylnicotinoyl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea

HRID 1697954Notes

Reaction equation

HRID 1697954 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.[CH2:12]([NH:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]=[C:26]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:27]3[CH2:33][CH2:32][NH:31][CH2:30][C:28]=3[N:29]=2)=[CH:20][CH:19]=1)=[O:16])[CH3:13]>>[CH2:12]([NH:14][C:15]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:25]=[C:26]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)[C:27]3[CH2:33][CH2:32][N:31]([C:4](=[O:6])[C:3]4[CH:7]=[CH:8][CH:9]=[N:10][C:2]=4[CH3:1])[CH2:30][C:28]=3[N:29]=2)=[CH:22][CH:23]=1)=[O:16])[CH3:13]

Participants

3

Reactant 2

HCID 6433732-Methylnicotinic acidHCID 671770581-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea hydrochloride salt

Product 1

HCID 592393991-Ethyl-3-(4-(7-(2-methylnicotinoyl)-4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)ureaYield 58%

Procedure

The compound oy was obtained following the general procedure in Example 213, substituting 3-methyloxetane-3-carboxylic acid for 2-methylnicotinic acid and substituting (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea hydrochloride salt (jk) for 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea hydrochloride salt (bf). The desired product oy (74 mg, 58% yield) was obtained as white solid: 1H NMR (400 MHz, DMSO) δ 8.64 (s, 1H), 8.20 (m, 2H), 7.42 (m, 2H), 6.15 (m, 1H), 4.61 (m, 2H), 3.82 (m, 1H), 3.73 (m, 4H), 3.49 (m, 5H), 3.20-3.04 (m, 2H), 2.76 (m, 2H), 2.53 (s, 3H, overlapping with DMSO peak), 1.06 (t, J=7.1 Hz, 3H); LC-MS m/z=502 (M+H).

Workup

  1. customThe compound oy was obtained

Sources & evidence

ORD record
ord-04dd70e16d094ca0bda5298c075d0475
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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