Dimethylformamide → HCID 59239247, compound

HRID 1698033Notes

Reaction equation

HRID 1698033 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.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>>[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[CH2:28][CH2:27][O:26][CH2:25][C@@H:24]3[CH2:29][CH3:30])[C:16]3[CH2:22][CH2:21][N:20]([S:46]([CH3:45])(=[O:48])=[O:47])[CH2:19][C:17]=3[N:18]=2)=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67178678HCID 67178678, compound

Product 1

HCID 59239247HCID 59239247, compound

Procedure

(S)-1-ethyl-3-(4-(4-(3-ethylmorpholino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0499 g, 0.122 mmol) in dry N,N-Dimethylformamide (0.60 mL, 7.7 mmol) was added N,N-Diisopropylethylamine (0.0636 mL, 0.365 mmol) followed by Methanesulfonyl chloride (0.01410 mL, 0.1822 mmol). The reaction mixture was stirred for 1 hour then submitted for purification. 1H NMR (400 MHz, DMSO) δ 8.65 (s, 1H), 8.16 (d, J=8.7, 2H), 7.48 (d, J=8.8, 2H), 6.18 (t, J=5.5, 1H), 4.32 (dd, J=36.6, 17.0, 2H), 4.01 (s, 1H), 3.85 (d, J=10.7, 1H), 3.79 (d, J=11.4, 1H), 3.68 (dd, J=20.5, 8.8, 2H), 3.59-3.49 (m, 2H), 3.43 (t, J=11.0, 1H), 3.26-3.17 (m, 1H), 3.16-3.06 (m, 2H), 3.02 (s, 3H), 2.94-2.81 (m, 1H), 2.77-2.63 (m, 1H), 1.88-1.69 (m, 2H), 1.06 (t, J=7.2, 3H), 0.83 (t, J=7.4, 3H). LC/MS-m/z+489.2 (M+H)+.

Workup

  1. customthen submitted for purification

Sources & evidence

ORD record
ord-28b28606c33347e2bbc0946c85c15a8e
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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