(S)-3-aminohexan-1-ol → (S)-methyl 1-(4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)-1H-imidazole-5-carboxylate

HRID 2207103Notes

Reaction equation

HRID 2207103 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:37]=[CH:36][C:25]([CH2:26][N:27]3[C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][N:29]=[CH:28]3)=[CH:24][C:23]=2[O:38][CH3:39])=[C:4]([CH3:40])[N:3]=1.[NH2:41][C@@H:42]([CH2:46][CH2:47][CH3:48])[CH2:43][CH2:44][OH:45]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:41][C@@H:42]([CH2:46][CH2:47][CH3:48])[CH2:43][CH2:44][OH:45])[C:5]([CH2:21][C:22]2[CH:37]=[CH:36][C:25]([CH2:26][N:27]3[C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][N:29]=[CH:28]3)=[CH:24][C:23]=2[O:38][CH3:39])=[C:4]([CH3:40])[N:3]=1

Participants

3

Reactant 2

HCID 11062353(S)-3-aminohexan-1-olHCID 117992731methyl 1-(4-((2-amino-4-(mesitylenesulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)-1H-imidazole-5-carboxylate

Product 1

HCID 117992589(S)-methyl 1-(4-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)-1H-imidazole-5-carboxylateYield 69%

Procedure

The sub-title compound was synthesized by the method of example 1 step (viii) from the product of step (i) (90 mg) and (s)-3-aminohexan-1-ol (56 mg). The sub-title compound (53 mg) was obtained as a colourless oil; LC-MS: m/z 483.

Sources & evidence

ORD record
ord-37f9f93df18343f08134ac25f7d482d9
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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