(S)-3-aminohexan-1-ol → (S)-ethyl 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-difluoroethyl)amino)acetate

HRID 2207070Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)[C:5]([CH2:21][C:22]2[CH:39]=[CH:38][C:25]([CH2:26][N:27]([CH2:34][CH:35]([F:37])[F:36])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][C:23]=2[O:40][CH3:41])=[C:4]([CH3:42])[N:3]=1.[NH2:43][C@@H:44]([CH2:48][CH2:49][CH3:50])[CH2:45][CH2:46][OH:47]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:43][C@@H:44]([CH2:48][CH2:49][CH3:50])[CH2:45][CH2:46][OH:47])[C:5]([CH2:21][C:22]2[CH:39]=[CH:38][C:25]([CH2:26][N:27]([CH2:34][CH:35]([F:36])[F:37])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][C:23]=2[O:40][CH3:41])=[C:4]([CH3:42])[N:3]=1

Participants

Reactant 2

HCID 11062353(S)-3-aminohexan-1-ol

HCID 117992778Ethyl 2-((4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-difluoroethyl)amino)acetate

Product 1

HCID 117999084(S)-ethyl 2-((4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)(2,2-difluoroethyl)amino)acetateYield 75.8%

Procedure

The sub-title compound was synthesized by the method of example 1 step (viii) from the product of step (ii) (520 mg) and (S)-3-aminohexan-1-ol (300 mg). The sub-title compound (340 mg) was obtained as a colourless gum; 1H NMR (CDCl3); 6.90-6.88 (2H, m), 6.78 (1H, d), 5.73 (1H, tt), 4.60 (1H, d), 4.55 (2H, br s), 4.15 (2H, q), 4.11-4.03 (1H, m), 3.88 (3H, s), 3.85 (2H, s), 3.66 (2H, s), 3.47-3.37 (3H, m), 3.25 (1H, ddd), 3.04 (2H, dt), 2.33 (3H, s), 1.83-1.73 (1H, m), 1.51-1.32 (3H, m), 1.25 (3H, t), 1.06-0.99 (2H, m), 0.73 (3H, t).

Sources & evidence

ORD record: ord-30e80aeca49e4001bf33fa90657b3bd0
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376398B2

Reaction notes

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