Dimethylformamide → HCID 59239174, compound

HRID 1698005Notes

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.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>>[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][N:22]([S:46]([CH3:45])(=[O:48])=[O:47])[CH2:21][CH2:20][C:18]=3[N:19]=2)=[CH:10][CH:9]=1)=[O:6])[CH3:3]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 31297Methanesulfonyl chloride

HCID 81531Diisopropylethylamine

HCID 67276185HCID 67276185, compound

Product 1

HCID 59239174HCID 59239174, 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 Methanesulfonyl chloride (0.0268 mL, 0.346 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=8.7, 2H), 7.49 (d, J=8.8, 2H), 6.18 (t, J=5.5, 1H), 4.23 (dd, J=31.8, 14.8, 2H), 3.97-3.91 (m, 1H), 3.88 (d, J=11.3, 1H), 3.72 (dd, J=11.4, 2.7, 1H), 3.62 (dd, J=10.0, 7.5, 3H), 3.49-3.38 (m, 3H), 3.16-3.08 (m, 2H), 3.03 (s, 3H), 2.99 (t, J=6.3, 2H), 1.22 (d, J=6.6, 3H), 1.06 (t, J=7.2, 3H). LC/MS-m/z+475.2 (M+H)+.

Workup

customThe reaction mixture was purified by HPLC

Sources & evidence

ORD record: ord-9d217446959140bcb14d69a8f9664b98
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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