Dimethylformamide → HCID 59239122, compound

HRID 1698030Notes

Reaction equation

HRID 1698030 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][C@@H:24]3[CH2:29][CH3:30])[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].CN(C)C=O.C(N(CC)C(C)C)(C)C.[C:45](Cl)(=[O:47])[CH3:46]>>[C:45]([N:20]1[CH2:21][CH2:22][C:16]2[C:15]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH2:29][CH3:30])=[N:14][C:13]([C:10]3[CH:9]=[CH:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:12][CH:11]=3)=[N:18][C:17]=2[CH2:19]1)(=[O:47])[CH3:46]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67178678HCID 67178678, compound

Product 1

HCID 59239122HCID 59239122, compound

Procedure

(S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.251 g, 0.611 mmol) in dry N,N-Dimethylformamide (3.00 mL, 38.7 mmol) was added N,N-Diisopropylethylamine (0.310 mL, 1.78 mmol) followed by Acetyl chloride (0.0650 mL, 0.913 mmol). The reaction mixture was stirred for overnight. The reaction mixture was purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.68 (s, 1H), 8.17 (d, J=7.6, 2H), 7.48 (d, J=7.9, 2H), 6.22 (d, J=6.1, 1H), 4.78-4.63 (m, 1H), 4.44 (dd, J=82.7, 18.2, 1H), 3.97 (s, 1H), 3.85 (d, J=11.1, 1H), 3.78 (d, J=11.6, 1H), 3.67 (d, J=7.4, 2H), 3.45 (dd, J=38.1, 25.8, 3H), 3.29 (m, 1H), 3.16-3.07 (m, 2H), 2.68 (dd, J=47.0, 37.1, 2H), 2.12 (s, 3H), 1.78 (ddd, J=27.5, 13.8, 7.0, 2H), 1.06 (t, J=7.2, 3H), 0.83 (dd, J=12.0, 7.4, 3H). LC/MS-m/z+453.2 (M+H)+.

Workup

  1. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-5e16d6b192f04d3c9d3e8726a975c01a
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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