Dimethylformamide → HCID 59239561, compound

HRID 1697959Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:16]3[CH2:22][CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].[CH:29](N(CC)C(C)C)([CH3:31])[CH3:30].[CH3:38][N:39]([CH3:42])[CH:40]=[O:41]>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[C:16]3[CH2:22][CH2:21][N:20]([C:38]4[N:39]([CH3:42])[C:40](=[O:41])[CH:30]=[CH:29][CH:31]=4)[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 469130711-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl) phenyl)urea

Product 1

HCID 59239561HCID 59239561, compoundYield 4.4%

Procedure

To a solution of 1-ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (bf) (115 mg, 0.300 mmol) in N,N-Dimethylformamide (2.00 mL) and N,N-Diisopropylethylamine (0.104 mL, 0.600 mmol) was added 6-chloror-1-methylpyridin-2(1H)-one (129 mg, 0.90 mmol) at room temperature. The reaction was kept at 140° C. overnight, followed by RPHPLC purification. The desired product pv (6.4 mg, 4.4% yield) was obtained as white powder: 1H NMR (400 MHz, DMSO) δ 8.64 (s, 1H), 8.19 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.8 Hz, 2H), 7.38 (m, 1H), 6.19-6.10 (m, 2H), 6.01 (d, J=6.6, 1H), 4.15 (s, 2H), 3.80-3.71 (m, 4H), 3.53 (m, 4H), 3.48 (s, 3H), 3.24-3.06 (m, 4H), 2.86 (s, 2H), 1.06 (t, J=7.2 Hz, 3H); LC-MS m/z=490 (M+H).

Workup

customfollowed by RPHPLC purification

Sources & evidence

ORD record: ord-c1058736d2b84043bbe688c16435d086
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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