Dimethylformamide → HCID 59239583, compound

HRID 1698006Notes

Reaction equation

HRID 1698006 reaction equation
Cl.[CH2:2]([NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]3[CH3:30])[C:17]3[CH2:23][NH:22][CH2:21][CH2:20][C:18]=3[N:19]=2)=[CH:10][CH:9]=1)=[O:6])[CH3:3].CN(C)C=O.C(N(CC)C(C)C)(C)C.[CH:45]1([S:48](Cl)(=[O:50])=[O:49])[CH2:47][CH2:46]1>>[CH:45]1([S:48]([N:22]2[CH2:21][CH2:20][C:18]3[N:19]=[C:14]([C:11]4[CH:12]=[CH:13][C:8]([NH:7][C:5]([NH:4][CH2:2][CH3:3])=[O:6])=[CH:9][CH:10]=4)[N:15]=[C:16]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][C@@H:25]4[CH3:30])[C:17]=3[CH2:23]2)(=[O:50])=[O:49])[CH2:47][CH2:46]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 67276185HCID 67276185, compound

Product 1

HCID 59239583HCID 59239583, compound

Procedure

(S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)phenyl)urea hydrochloride (0.1000 g, 0.2310 mmol) in dry N,N-Dimethylformamide (1.60 mL, 20.7 mmol) was added N,N-Diisopropylethylamine (0.161 mL, 0.924 mmol) followed by Cyclopropanesulfonyl chloride (0.0354 mL, 0.347 mmol). The reaction mixture was stirred for 2 hours. The reaction mixture was purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.69 (s, 1H), 8.19 (d, J=8.8, 2H), 7.49 (d, J=8.8, 2H), 6.18 (t, J=5.6, 1H), 4.31 (q, J=15.1, 2H), 3.89 (dd, J=12.2, 9.2, 2H), 3.75-3.52 (m, 5H), 3.44 (d, J=5.0, 2H), 3.19-3.05 (m, 2H), 2.99 (d, J=3.7, 2H), 2.75-2.66 (m, 1H), 1.24 (d, J=6.6, 3H), 1.06 (t, J=7.2, 3H), 0.93 (dt, J=13.8, 5.5, 4H). LC/MS-m/z+501.2 (M+H)+.

Workup

  1. customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record
ord-49ec16220b3a45f3905f60a9fb95dc24
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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