Ethyl 2-(ethylamino)acetate → (S)-ethyl 2-((3-(4-((4-(1-acetoxyhexan-3-ylamino)-2-amino-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenoxy)propyl)(ethyl)amino)acetate

HRID 2207097Notes

Reaction equation

[C:1]([O:4][CH2:5][CH2:6][C@@H:7]([NH:11][C:12]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28]OS(C)(=O)=O)=[CH:21][C:20]=2[O:34][CH3:35])=[C:16]([CH3:36])[N:15]=[C:14]([NH2:37])[N:13]=1)[CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2].[CH2:38]([NH:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH3:39]>>[C:1]([O:4][CH2:5][CH2:6][C@@H:7]([NH:11][C:12]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][N:40]([CH2:38][CH3:39])[CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:21][C:20]=2[O:34][CH3:35])=[C:16]([CH3:36])[N:15]=[C:14]([NH2:37])[N:13]=1)[CH2:8][CH2:9][CH3:10])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 12591597Ethyl 2-(ethylamino)acetate

HCID 89906963(S)-3-(2-amino-5-(2-methoxy-4-(3-(methylsulfonyloxy)propoxy)benzyl)-6-methylpyrimidin-4-ylamino)hexyl acetate

Product 1

HCID 118000980(S)-ethyl 2-((3-(4-((4-(1-acetoxyhexan-3-ylamino)-2-amino-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenoxy)propyl)(ethyl)amino)acetate

Procedure

The sub-title compound was synthesized by the method of example 9 step (vi) from the product of example 9 step (v) (75 mg) and the product of example 1 step (vi). The sub-title compound (60 mg) was obtained as a pale yellow oil; 1H NMR (300 MHz, CDCl3); 6.81 (1H, d), 6.44 (1H, d), 6.38 (1H, dd), 4.95 (2H, br s), 4.28-4.05 (3H, m), 4.00-3.85 (4H, m), 3.85 (3H, s), 3.57 (2H, s), 3.32 (2H, s), 2.77-2.62 (4H, m), 2.36 (3H, s), 1.97 (3H, s), 1.95-1.72 (3H, m), 1.63-1.50 (1H, m), 1.48-1.33 (1H, m), 1.30-1.15 (2H, m), 1.24 (3H, t), 1.11-0.98 (2H, m), 1.03 (3H, t), 0.77 (3H, t); LC-MS: m/z 574.

Sources & evidence

ORD record: ord-9f0c458042c04de89a0c701cfbdb89b3
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376398B2

Reaction notes

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